Name: 1809-10-5|3-Bromopentane|97%
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1
[ 1809-10-5 ]
[ 24155-42-8 ]
1-[2-(2,4-Dichloro-phenyl)-2-(1-ethyl-propoxy)-ethyl]-1H-imidazole [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1998,vol. 32,p. 1001 - 1007

2
[ 1809-10-5 ]
[ 108-98-5 ]
[ 13921-09-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With n-butyllithium In tetrahydrofuran; hexane for 0.333333h; Ambient temperature;
87%	Stage #1: thiophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20 - 70℃; for 0.5h; Inert atmosphere; Stage #2: 3-bromopentane In N,N-dimethyl-formamide; mineral oil at 80℃; for 1h; Inert atmosphere;
63%	Stage #1: thiophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3-bromopentane In N,N-dimethyl-formamide; mineral oil at 80℃; for 1h; Inert atmosphere;	4.2 General procedure for the synthesis of compounds 2-4 General procedure: Thiophenol (1.76g, 16mmol) was added to a suspension of sodium hydride (60% suspension in mineral oil, 0.7g, 18mmol) in anhydrous DMF (15mL) under an argon atmosphere, and the mixture was stirred at rt for 30min. A solution of the particular alkylbromide (16mmol) dissolved in DMF (11mL) was then added. The resulting mixture was heated at 80°C for 1h, and then, water (45mL) was added after cooling. The mixture was transferred to a separatory funnel and washed with diethyl ether (3×25mL). The organic phase was dried over Na2SO4, evaporated and purified by column chromatography on silica with hexane as the mobile phase.

With potassium carbonate In N,N-dimethyl-d<SUB>6</SUB>-formamide Reflux;

I. Preparation of isopropyl sulfides General procedure: Thiophenols/thiols were commercially available. In general, isopropyl sulfides were prepared according to the literature1 (phenyl isopropyl sulfide was purchased commercially). 1.2 equiv. of isopropyl bromides (for 1j, 2.4 equiv. of isopropyl bromide is added) were added to a dry N,N-dimethylformamide (10 ml) of thiophenols/thiols (7.8 mmol) and anhydrous K2CO3 (11.7 mmol). The mixture was heated at reflux overnight. After completion, the reaction mixture was cooled to room temperature and extracted with diethyl ether (30 ml × 3), then the organic phase was washed with brine, dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. Then the residue was purified by flash column chromatography on silica gel (petroleum ether) to afford the desired sulfides.

Reference： [1]Yin, Jianming; Pidgeon, Charles [Tetrahedron Letters, 1997, vol. 38, # 34, p. 5953 - 5954]
[2]Scholz, Roland; Hellmann, Gunther; Rohs, Susanne; Raabe, Gerhard; Runsink, Jan; Oezdemir, Diana; Luche, Olaf; Hess, Thomas; Giesen, Alexander W.; Atodiresei, Juliana; Lindner, Hans J.; Gais, Hans-Joachim [European Journal of Organic Chemistry, 2010, # 24, p. 4559 - 4587]
[3]Nawrot, Daria; Kolenič, Marek; Kuneš, Jiří; Kostelansky, Filip; Miletin, Miroslav; Novakova, Veronika; Zimcik, Petr [Tetrahedron, 2018, vol. 74, # 5, p. 594 - 599]
[4]Yan, Xiaojing; Li, Chang; Xu, Xiaofei; He, Quan; Zhao, Xiaoyong; Pan, Yuanjiang [Tetrahedron, 2019, vol. 75, # 23, p. 3081 - 3087]

3
4-(2,4-dimethylphenyl)-2-methyl-1,2-dihydro-3H-indazol-3-one [ No CAS ]
[ 1809-10-5 ]
4-(2,4-dimethylphenyl)-1-(1-ethylpropyl)-2-methyl-1,2-dihydro-3H-indazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: 4-(2,4-dimethylphenyl)-2-methyl-1,2-dihydro-3H-indazol-3-one; 3-bromopentane With sodium hydride In N,N-dimethyl-formamide at 20℃; for 48h; Stage #2: With water In N,N-dimethyl-formamide	21 To a solution containing 0.008 g (0.03 mmol) of 4- (2,4-dimethylphenyl)-2-methyl-1,2-dihydro-3H-indazo3.-3-one in 2 ml of N,N-dimethylformamide under a nitrogen atmosphere was added 0.001 g (0.038 mmol) of sodium hydride followed by 0.007 g (0.048 mmol) of 3-bromo-pentan e. The reaction was allowed to stir at room temperature for 48h, quenched with water and extracted with ethyl acetate. The organic phase was dried over magnesium s ulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 25% ethyl a cetate/ dichloromethane gave 0.003 g (30%) of compound. ¹H NMR (CDC13) No.: 0.90 - 0. 95 (m, 6H) , 1. 68 - 1.82 (m, 4H), 2.13 (s, 3H), 2.36 (s, 3H), 3.39 (s, 3H), 3.64 - 3.71 (m, 1H), 6.89 (d, J = 7.2 Hz, 1H), 7.03 - 7.15 (m, 4H), 7.46 (t, J = 8.3 Hz, 1H). MS Calcd. : 322; Found: 323 (M+H).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2005/99688, 2005, A2 Location in patent: Page/Page column 180-181

4
[ 868372-54-7 ]
[ 1809-10-5 ]
2-[(1-ethylpropyl)amino]-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With sodium hydride In N,N-dimethyl-formamide at 0 - 60℃; for 67.4167h;	51 To a solution of 2-amino-5-mesityl-3,7-dimethyl-3,7- dihydro-4H-pyrrolo [2,3-d]pyrimidin-4-one (0.062 g, 0.209 mmol) in N, N-dimethylformamide (0.5 mL) was added sodium hydride (66 % in oil, 0.016 g, 0.439 mmol), and the mixture was allowed to stir at room temperature for 25 minutes. 3- Bromopentane (0.055 mL, 0.439 mmol) twice at room temperature and sodium hydride (66 % in oil, 0.016 g, 0.439 mmol) at 0 °C was added during the reaction, stirring at room temperature for 15 hours and at 60 °C for 52 hours. After cooling, the reaction mixture was diluted with ice- cold water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with hexane/ethyl acetate (4:1 - 2:1). The desired fractions were concentrated in vacuo. The residual crystals were washed with diisopropyl ether-hexane to give 0.019 g (25%) of the title compound. mp 174-176 °C. ¹H NMR (CDC13) 5: 0.98 (t, J = 7.5 Hz, 6H), 1.50-1.77 (m, 4H), 2.11 (s, 6H), 2.28 (s, 3H), 3.37 (s, 3H), 3. 65 (s, 3H), 4.03-4.14 (m, 2H), 6.30 (s, 1H), 6.90 (s, 2H).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2005/99688, 2005, A2 Location in patent: Page/Page column 226-227

5
[ 868373-84-6 ]
[ 1809-10-5 ]
1-mesityl-4-(3-pentylamino)-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With sodium hydride In N,N-dimethyl-formamide at 80℃; for 15h;	107 To a slution of 4-amino-1-mesityl-6-methyl-1,6- dihydro-7H-pyrrolo [2, 3-d]pyridazin-7-one (113 mg, 0.40 mmol) in DMF (1 ml) were added sodium hydride (60% in oil, 48 mg, 1.20 mmol) and 3-bromopentane (0.15 ml, 1.20 mmol). The mixture was stirred at 80 °C for 15 hours, then diluted with water (30 ml) and extracted with ethyl acetate (50 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with hexane/ethyl acetate (5: 1) to give 35 mg (25%) of the title compound as crystals. mp 183 - 185 °C. ¹H NMR (CDC13) 5: 0.99 (6H, t, J = 7.4 Hz), 1.50 -1.80 (4H, m), 1.93 (6H, s), 2.32 (3H, s), 3.60 (3H, s), 3.75 - 3.90 (2H, m) , 6.42 (lH, d, J = 3.0 Hz) , 6.93 (lH, d, J = 3. 0 Hz) , 6.94 (2H, brs).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2005/99688, 2005, A2 Location in patent: Page/Page column 266-267

6
[ 1809-10-5 ]
[ 178268-92-3 ]
[ 949536-04-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5218 - 5221

7
[ 1809-10-5 ]
[ 616-31-9 ]

Yield	Reaction Conditions	Operation in experiment
5%	Stage #1: 3-bromopentane With thiourea In ethanol for 2h; Heating / reflux; Stage #2: With sodium hydroxide; water at 20℃; for 18h;	14 Preparation 14; Pentane-3-thiol; Thiourea (3.03g, 40mmol) was added to a solution of 3-bromopentane (5g, 33mmol) in ethanol (4OmL) and the mixture was heated under reflux for 2 hours. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (3OmL), 5M sodium hydroxide solution (15mL, 75mmot) was added and the mixture was stirred at room temperature for 18 hours The reaction mixture was acidified with 15% sulfuric acid and partitioned between pentane (10OmL) and water (5OmL). The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo to afford the title compound in 5% yield, 200mg.1HNMR(400MHz, CDCI3) δ 0 97-1.01 (m, 6H), 1 30-1 32(m, 1 H), 1 44-1 55(m, 2H), 1.62-1 74(m, 2H), 2 62-2 70(m, 1 H)
	Multi-step reaction with 2 steps 1: ethanol / Heating 2: NaOH / ethanol / 2 h / Heating

Reference： [1]Current Patent Assignee: PFIZER INC - WO2007/57756, 2007, A2 Location in patent: Page/Page column 34
[2]Smaldone, Ronald A.; Moore, Jeffrey S. [Journal of the American Chemical Society, 2007, vol. 129, # 17, p. 5444 - 5450]

8
3-cyano-6-(3-hydroxycarbonyl)-4-(2-fluorobenzyl)-2-(4-hydroxyphenyl)-1-{N-methyl-N-[2-(2-pyridyl)ethyl]amino}methylpyrrolo[1,2-a]pyrimid-7-one [ No CAS ]
[ 1809-10-5 ]
[ 308143-13-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 90℃; Heating / reflux;	64.B Example 64 3-Cyano-6-(3-pentoxycarbonyl)-4-(2-fluorobenzyl)-2-[4-(3 -pentoxyphenyl]-1-methylpyrrolo[1,2-a]pyrimid-7-one To a stirred solution of 3-Cyano-6-(3-hydroxycarbonyl)-4-(2-fluorobenzyl)-2-(4-hydroxyphenyl)-1-methylpyrrolo[1,2-a]pyrimid-7-one (83 mg, 0.2 mmol) in dry DMF (5 mL) under atmosphere of N2, potassium carbonate (500 mg, 3.6 mmol.) was added, followed by addition of 3-bromopentane (0.5 mL, 4.0 mmol.). The slurry was heated at 900 C. overnight and treated with ethyl acetate (20 mL) and water (20 mL). The organic layer was separated and filtered through a silica gel pad (10 g), washed with ethyl acetate. It was then concentrated to give the titled product, essentially pure by TLC (85 mg, 76%). MS: 558 (MH+).

Reference： [1]Current Patent Assignee: NEUROCRINE BIOSCIENCES INC - US6346534, 2002, B1 Location in patent: Page column 36

9
[ 1809-10-5 ]
[ 713147-45-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 0.75h; Stage #2: 3-bromopentane With potassium carbonate In acetonitrile for 12h; Heating / reflux;	Example 12 (General procedure (A)) /Step B/1 Step B: The above nitrile (9.2 g, 41 MMOL) was dissolved in DICHLOROMETHANE (50 mL) and trifluoroacetic acid (15 mL) was added. The mixture was stirred for 45 min at ambient tem- perature and then the solvent was evaporated. The residue was dissolved in acetonitrile (200 mL) and with stirring, excess potassium carbonate was added. The mixture was filtered and the solvent was evaporated. The oily residue was dissolved in acetonitrile (150 mL) and 3- pentylbromide (15.6 g, 105 MMOL) and potassium carbonate (25.5 g, 185 MMOL) were added and the reaction mixture was stirred at reflux temperature overnight. The mixture was al- lowed to cool, then filtered and the solvent evaporated. The residue was dissolved in ethyl acetate (200 mL) and the organic phase was washed with water (20 mL). The organic phase was dried (MGS04) in the presence of activated carbon, filtered and the solvent was evapo- rated. This afforded 7.8 g of crude 2- (1- (1-ETHYLPROPYL) PIPERIDIN-4-YL) ACETONITRILE.

Reference： [1]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2004/54973, 2004, A2 Location in patent: Page 38

10
[ 701267-20-1 ]
[ 1809-10-5 ]
[ 701267-21-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With caesium carbonate In DMF (N,N-dimethyl-formamide) at 80℃;	214 Example 214 To a solution under Ar of (RS)-N- (4-CYANO-BENZYL)-2- (2, 6-DIFLUORO-3-HYDROXY-PHENYL)-2- ethoxy-acetamide (200 mg) in DMF (10 ml) was added CSC03 (226 mg) and 3- bromopentane (105 mg). The solution was stirred over night at 80 °C. The solvent was evaporated and the residue was taken up in H20 (50 ml). The product was extracted with AcOEt (2 x 100 ml). The organic layers were washed with HZO (2 x 50 ml) and dried (NAAS04) and the solvent was evaporated. CC (AcOEt/Hept 2: 3 to AcOEt) afforded 190 mg (79 %) of (RS)-N- (4-CYANO-BENZYL)-2-ETHOXY-2- [3- (L-ETHYL-PROPOXY)-2, 6-difluoro- phenyl]-acetamide. This material was converted to (RS)-N- (4-CARBAMIMIDOYL-BENZYL)-2- ETHOXY-2- [3- (1-ETHYL-PROPOXY)-2, 6-DIFLUORO-PHENYL]-ACETAMIDE acetate by the sequence of procedures G and H. Off-white solid. MS 434.4 ([M+H] +).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2004/48335, A2 Location in patent: Page 126-127

11
[ 791782-89-3 ]
[ 1809-10-5 ]
2-(1'-ethylpropyloxy)-6-decyl-2,3-dihydrofuro[2,3-d]pyrimidine [ No CAS ]
3-(1'-ethylpropyl)-6-decyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 43% 2: 27%	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20 - 120℃; for 4.5h;	26 (0.50 g, 1.81 mmol), potassium carbonate (0. 50 g, 3.62 mmol, 2 equiv) and 3- bromopentane 42 (0.45 mL, 3.62 mmol, 2 equiv. ) were suspended in dry DMF (15 mL) under N2, and the reaction mixture heated to 120 °C with stirring for 150 min. The dark suspension was allowed to cool to RT over 2 h, and then the solvent was removed under reduced pressure at 80 °C. The residue was then subjected to flash column chromatography purification in a 0-5 % MEOH/DCM eluent gradient to yield 43 as a yellow oil of weight 0.27 g (43 % yield). IH NMR (CDC13) 8 = 8.44 (s, 1H, 4-H), 6.20 (s, 1H, 5-H), 4.96 (qt, 1H, J= 6.0 Hz, 1 -H), 2.60 (t, 2H, J= 7.5 Hz, A-CH2), 1. 68-1. 55 (m, 6H, 3 x CH2), 1.24-1. 13 (m, 12H, 6 x CHEZ), 0.84 (t, 6H, J = 7.4 Hz, 2 x CH3), 0.74 (t, 3H, J = 6.9 Hz, CH3) ; 13C NMR (CDCl3) 8 = 168.8 (7a-C), 162.9 (6-C), 158.7 (2-C), 150.9 (4-CH), 113.9 (4a-C), 99.5 (5-CH), 79.9 (1 - CH), 32.2 (CH2), 29.9 (CH2), 29.7 (CH2), 29.6 (CH2), 29.4 (CH2), 28.7 (CH2), 27.6 (CH2), 26.7 (2 x CH2), 26.4 (CH2), 23.0 (CH2), 14.4 (CH3), 9.9 (2 x CH3). Elemental analysis calcd for C2LH34N202 (346.5) : C 72.79, N 8.08, H 9.89 ; found C 73.12, N 8.56, H 9.93. 3- (1 -ETHYL-PROPYL)-6-DECYL-2, 3-dihydrofuro [2, 3-0PYRIMIDIN-2-ONE CF2253 Also isolated from the above reaction was the title compound 44 as a white solid (0.168 g, 27%). 'H NMR (CDC13) 5 = 7.72 (s, 1H, 4-H), 6.15 (s, 1H, 5-H), 4.94 (b, 1H, 1 -H), 2.67 (t, 2H, J = 7. 4 Hz, a-CH2), 1.87 (M, 2H, CH2), 1.71 (m, 4H, 2 x CH2), 1.36-1. 23 (m, 14H, 7 x CH2), 0.91 (t, 9H, J= 6.8 Hz, 3 x CH3) ; 13C NMR (CDCL3) No. = 171.2 (7A-C), 160.4 (6-C), 156.7 (2-C), 135.5 (4-CH), 108.3 (4A-C), 98.9 (5-CH), 32.3 (CH2), 30.0 (CH2), 29.9 (CH2), 29.7 (2 x CH2), 29.5 (CH2), 28.7 (CH2), 28.0 (CH2), 27.2 (CH2), 23.1 (CH2), 14.5 (CH3), 10.8 (2 x CH3). Elemental analysis calculated for C2LH34N202 (346.5) : C 72.79, N 8.08, H 9.89 ; found C 72.65, N 8.16, H 10.08.

Reference： [1]Current Patent Assignee: CARDIFF UNIVERSITY; KATHOLIEKE UNIVERSITEIT LEUVEN - WO2004/96813, 2004, A1 Location in patent: Page 29-30

12
[ 5900-58-3 ]
[ 124-09-4 ]
[ 5162-44-7 ]
[ 446-48-0 ]
[ 7209-38-3 ]
[ 74-96-4 ]
[ 4784-77-4 ]
[ 22288-78-4 ]
[ 542-69-8 ]
bromomethyl resin [ No CAS ]
9-fluorenyl-methoxycarbonyl-cyclohexyl alanine [ No CAS ]
[ 462-94-2 ]
[ 1458-98-6 ]
[ 78-77-3 ]
[ 1809-10-5 ]
[ 110-53-2 ]
[ 592-55-2 ]
[ 7328-91-8 ]
[ 871-76-1 ]
[ 105-83-9 ]
[ 144-48-9 ]
[ 929-59-9 ]
[ 107-59-5 ]
[ 5324-30-1 ]
[ 5428-54-6 ]
[ 27129-86-8 ]
[ 2417-72-3 ]
[ 2581-34-2 ]
[ 554-84-7 ]
[ 3385-21-5 ]
[ 126-38-5 ]
[ 636-93-1 ]
[ 88-30-2 ]
[ 620-13-3 ]
[ 823-78-9 ]
[ 5035-82-5 ]
[ 29022-11-5 ]
[ 539-48-0 ]
[ 35661-39-3 ]
[ 26759-46-6 ]
[ 20439-47-8 ]
[ 2615-25-0 ]
[ 6393-01-7 ]
[ 5372-81-6 ]
[ 35661-40-6 ]
[ 100-39-0 ]
[ 611-17-6 ]
[ 23915-07-3 ]
[ 71989-23-6 ]
[ 35737-15-6 ]
[ 2592-95-2 ]
[ 18880-00-7 ]
[ 88681-68-9 ]
[ 100063-22-7 ]
[ 75-03-6 ]
[ 106-94-5 ]
[ 104-81-4 ]
[ 589-10-6 ]
[ 107-15-3 ]
[ 109-76-2 ]
[ 110-60-1 ]
[ 7051-34-5 ]
[ 106-95-6 ]
[ 622-95-7 ]
[ 589-15-1 ]
[ 134-20-3 ]
[ 2550-36-9 ]
[ 89-92-9 ]
[ 456-41-7 ]
[ 766-80-3 ]
[ 459-46-1 ]
[ 874-98-6 ]
[ 402-49-3 ]
[ 870-63-3 ]
[ 85118-01-0 ]
[ 22115-41-9 ]
[ 3958-57-4 ]
[ 100-11-8 ]
[ 107-82-4 ]
[ 6482-24-2 ]
[ 3132-64-7 ]
[ 112883-41-7 ]
[ 3433-80-5 ]
[ 52727-57-8 ]
C₁₈H₁₅N₂O₃PolS [ No CAS ]
C₂₀H₂₀N₃OPolS [ No CAS ]
C₂₃H₁₉N₂O₂PolS [ No CAS ]
C₁₈H₂₃ClN₃OPolS [ No CAS ]
C₂₂H₂₆N₃OPolS [ No CAS ]
C₂₂H₂₃N₂O₅PolS [ No CAS ]
C₂₀H₂₆ClN₂O₃PolS [ No CAS ]
C₂₃H₂₂ClN₂O₃PolS [ No CAS ]
C₂₀H₂₁FN₃O₃PolS [ No CAS ]
C₂₂H₂₉N₂O₃PolS [ No CAS ]
C₂₁H₂₈N₃O₃PolS [ No CAS ]
C₁₉H₂₆N₃O₄PolS₂ [ No CAS ]
C₂₂H₃₀N₃OPolS [ No CAS ]
C₂₁H₂₈N₃O₄PolS [ No CAS ]
C₂₆H₂₆N₃OPolS [ No CAS ]
C₂₃H₁₅ClF₃N₂O₂PolS [ No CAS ]
C₂₄H₂₂N₃O₃PolS [ No CAS ]
C₂₃H₁₆ClF₂N₂O₂PolS [ No CAS ]
C₂₂H₂₂Br₂N₃OPolS [ No CAS ]
C₂₄H₂₆FN₂O₅PolS [ No CAS ]
C₂₅H₂₂FN₂O₄PolS [ No CAS ]
C₂₆H₂₂N₃O₄PolS [ No CAS ]
C₂₅H₂₅ClN₃O₃PolS [ No CAS ]
C₂₅H₁₈ClF₂N₂O₃PolS [ No CAS ]
C₂₉H₂₆N₃O₃PolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; Carbonyldiimidazole; tin-2-ethylhexanoate dihydrate; potassium tert-butylate; water; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; diisopropyl-carbodiimide; dibromotriphenylphosphorane; In DMF (N,N-dimethyl-formamide); dichloromethane; N,N-dimethyl acetamide; 1,2-dichloro-ethane;Combinatorial reaction / High throughput screening (HTS);	EXAMPLE 1 [0213] This example shows the synthesis of a combinatorial library of thioquinazolinone derivatives. [0214] Step 1a: Preparation of Wang Bromide Resin [0215] 40 tea bags containing 2 g each of Wang resin (80 g, 120 mmol) was taken in a 5 L PP container. A solution of triphenylphosphine dibromide (152 g, 0.15 M, 3 eq., 360 mmol) in 2000 ml DCM was added and the solution was shaken at room temperature overnight. The resin was sequentially washed with DCM (4×, 1.5 L each) and diethylether (6×, 1.5 L each) and dried under vacuum, to give the bromo wang resin. [0216] Step 1b: Loading of the Nitrophenol on Bromo Wang [0217] 20 g of the Bromo wang resin (1.5 meq/g) was taken in a 2 L wide-mouthed glass container and 1000 mL DMA was addded to it followed by the addition of the nitro phenol (10 eq., 0.3M, 300 mmol). Potasium t-butoxide (33.46 g, 10 eq., 300 mmol) was then added to it and the bottles were heated at 50 C. overnight. The bags were washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The tea bags were then dried overnight in air. The following nitrophenols were used: [0218] 2-METHYL-5-NITROPHENOL [0219] 5-HYDROXY-2-NITROBENZOTRIFLUORIDE [0220] 3-METHYL-4-NITROPHENOL [0221] 2-METHOXY-5-NITROPHENOL [0222] M-NITROPHENOL [0223] Step 1c: Reduction of the Nitro Group to Amine [0224] A 2.0 M solution of tin-2-ethylhexanoate dihydrate was prepared in DMF containing 0.5% H2O. The tea bags were added and the solution is heated at 50 C. for 40 hours. After cooling the bags are washed with DMF/10% HOAc (3×), DMF (3×), 5% DIEA/DCM (2×), DCM (2×) and MeOH (2×) and dried in air overnight. [0225] Step 1d: Coupling N-FMOC Protected Amino Acid to Wang Resin. [0226] 20 g of Wang resin (1.5 meq/g) was placed in a porous polypropylene packet (Tea-bag, 60 mm×60 mm, 65mu) and taken in a 1000 mL plastic bottle. DMF (300 mL), DCM (300 mL), FMOC-Cyclohexyl alanine (70.82 g, 6 eq., 0.3M, 180 mmol), DIC (22.71 g, 6 eq., 180 mmol), HOBt (24.32 g, 6 eq., 180 mmol) were added sequentially. After shaking for 12 hours, the packet was washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The packet was then dried overnight in air. The tea bags containing the amino acids were then treated with 20% piperidine/DMF for 2 h at room temperature to deblock the FMOC group. The following amino acids were used: [0227] FMOC-GLY-OH [0228] FMOC-ALA-OH [0229] FMOC-L-ISOLEUCINE [0230] FMOC-L-PHENYLALANINE [0231] FMOC-D-NLE-OH [0232] FMOC-CHA-OH [0233] FMOC-L-TRYPTOPHAN [0234] Step 1e: Coupling of the Diamines to Wang Resin [0235] 20 g of Wang resin (1.5 meq/g) was placed in a porous polypropylene packet (Tea-bag, 60 mm×60 mm, 65mu) and taken in a 1000 mL Nalgene bottle. 600 mL of DCM was added followed by the addition of the carbonyl diimidazole (29.9 g, 6 eq., 0.3M, 180 mmol) and the flasks were shaken at room temperature for 3 hours after which they were decanted and washed with DCM (2×, 600 mL). To these Nalgene bottles were added the diamines (6 eq., 0.4M, 180 mmol) in 450 mL of DCM (0.4M) and they were shaken at room temperature overnight. The diamines used were as follows: [0236] 2,2-DIMETHYL-1,3-PROPANEDIAMINE [0237] 1,3-CYCLOHEXANEDIAMINE [0238] (1R,2R)-(-)-1,2-DIAMINOCYCLOHEXANE [0239] TRANS-1,4-DIAMINOCYCLOHEXANE [0240] P-XYLYLENEDIAMINE [0241] 1,4-BIS(3-AMINOPROPYL)PIPERAZINE [0242] ETHYLENEDIAMINE [0243] 1,3-DIAMINOPROPANE [0244] 1,8-DIAMINO-3,6-DIOXAOCTANE [0245] 1,4-DIAMINOBUTANE [0246] 1,5-DIAMINOPENTANE [0247] 1,6-HEXANEDIAMINE [0248] N,N-BIS(3-AMINOPROPYL)METHYLAMINE [0249] 2,2'-THIOBIS(ETHYLAMINE) [0250] 2,5-DIMETHYL-1,4-PHENYLENEDIAMINE [0251] After shaking overnight, the packets was washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The packet was then dried in air. [0252] Step 2: Formation of the Isothiocyanate [0253] The o-amino benzoate ester (136 g, 10 eq., 900 mmol) was taken in a 5 L wide-mouthed glass bottle and 2.7 L of dichloroethane was added to it (0.3M). The following esters were used: [0254] METHYL ANTHRANILATE [0255] METHYL 2-AMINO-4-CHLOROBENZOATE [0256] 2-AMINO-4,5-DIMETHOXYBENZOIC ACID [0257] METHYL ESTER [0258] METHYL 3,4,5-TRIMETHOXYANTHRANILATE [0259] DIMETHYL AMINOTEREPHTHALATE [0260] METHYL 2-AMINO-5-BROMOBENZOATE [0261] METHYL 3-AMINOTHIOPHENE-2-CARBOXYLATE [0262] METHYL 3-AMINO-5-PHENYLTHIOPHENE-2-CARBOXYLATE [0263] Thiocarbonyl diimidazole (160 g, 10 eq., 900 mmol) was added to it and the solution was heated at 55 C. overnight to form the isothiocyanate. [0264] Step 3: Formation of the Thioquinazolinone [0265] The next day the tea bags containing the amino acids, diamines and the amino phenols on wang resin (90 mmol) was added to the isothiocyanate solution from reaction 2 and the glass bottles were heated at 55 C. overnight. After cooling the bags was washed alternatively with DMF (2000 mL) and DCM (2000 mL) 3 cycles followed by 6 cycles of MeOH...

Reference： [1]Patent: US2004/102629,2004,A1 .Location in patent: Page 16-18

13
[ 955919-42-3 ]
[ 1809-10-5 ]
[ 885132-80-9 ]
[ 885132-79-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 3.7% 2: 11%	With potassium carbonate In N,N-dimethyl-formamide at 60 - 120℃; for 54h;	52 3-ethyl-6- { 1 -[4-(methylsulfonyl)phenyl] - 1 H-pyrazol-5-yl } - 1 H-indazole ( 100 mg, 0.27 mmol), 3-bromopentane (70 mg, 0.46 mmol), potassium carbonate (45 mg, 0.33 mmol) and N,N-dimethylformamide (2 mL) were added to a 1 -necked flask. The mixture was heated to 60 0C for 6 hours, then slowly cooled to room temperature and stirred for a further 48 hours. A further equivalent of 3-bromopentane (41 mg, 0.27 mmol) was then added, and the reaction was heated to 120 0C. After cooling to room temperature, water and ethyl acetate were added. The product was extracted once with ethyl acetate, and washed with water and brine. The combined organics were dried, and filtered and concentrated. The reside was purified by column chromatography on silica gel (eluting using 50% ethyl acetate in hexanes for 10 minutes and then a linear gradient to 100% ethyl acetate in hexanes at 20 minutes) to give 4.4 mg (3.7%) of 3-ethyl-2-(l- ethylpropyl)-6- { 1 -[4-(methylsulfonyl)phenyl]- 1 H-pyrazol-5-yl} -2H-indazole. LC/MS (EI) tR 4.36 (Method C), m/z 437.1 (M++l), 1H NMR (CDCl3) δ 0.6 (t, 3H), 1.4 (t, 2H), 1.8 (m, 2H), 1.9 (m, 2H), 3.0 (m, 6H), 4.0 (m, IH), 6.5 (s, IH), 7.0 (d, IH), 7.1 (s, IH), 7.5 (d, 2H), 7.7 (m, IH), 7.8 (s, IH), 7.8 (d, 2H). 13 mg (11%) of the corresponding EPO isomer (3-ethyl-l-(l-ethylpropyl)-6-{l-[4-(methylsulfonyl)phenyl]-lH-pyrazol-5-yl}- lH-indazole) was also isolated.
1: 11% 2: 3.7%	With potassium carbonate In N,N-dimethyl-formamide at 60 - 120℃; for 54h;	48 Example 48 3-Ethyl-2-(1-ethylpropyl)-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-2H-indazole 3-ethyl-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1H-indazole (100 mg, 0.27 mmol), 3-bromopentane (70 mg, 0.46 mmol), potassium carbonate (45 mg, 0.33 mmol) and N,N-dimethylformamide (2 mL) were added to a 1-necked flask. The mixture was heated to 60° C. for 6 hours, then slowly cooled to room temperature and stirred for a further 48 hours. A further equivalent of 3-bromopentane (41 mg, 0.27 mmol) was then added, and the reaction was heated to 120° C. After cooling to room temperature, water and ethyl acetate were added. The product was extracted once with ethyl acetate, and washed with water and brine. The combined organics were dried, and filtered and concentrated. The reside was purified by column chromatography on silica gel (eluting using 50% ethyl acetate in hexanes for 10 minutes and then a linear gradient to 100% ethyl acetate in hexanes at 20 minutes) to give 4.4 mg (3.7%) of 3-ethyl-2-(1-ethylpropyl)-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-2H-indazole. LC/MS (EI) tR 4.36 (Method C), m/z 437.1 (M++1), 1H NMR (CDCl3) δ0.6 (t, 3H), 1.4 (t, 2H), 1.8 (m, 2H), 1.9 (m, 2H), 3.0 (m, 6H), 4.0 (m, 1H), 6.5 (s, 1H), 7.0 (d, 1H), 7.1 (s, 1H), 7.5 (d, 2H), 7.7 (m, 1H), 7.8 (s, 1H), 7.8 (d, 2H). 13 mg (11%) of the corresponding isomer (3-ethyl-1-(1-ethylpropyl)-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1H-indazole) was also isolated.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2006/44528, 2006, A1 Location in patent: Page/Page column 162-163
[2]Current Patent Assignee: ROCHE HOLDING AG - US2007/254913, 2007, A1 Location in patent: Page/Page column 56

14
[ 1809-10-5 ]
5-(6-(2,6-dimethyl-4-(pentan-3-yloxy)phenyl)-2-(pyrazin-2-yl)pyrimidin-4-yl)-N-propylthiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	Stage #1: 3,5-dimethyl-4-(6-(2-(propylamino)thiazol-5-yl)-2-(pyrazin-2-yl)pyrimidin-4-yl)phenol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0333333h; Stage #2: 3-bromopentane In N,N-dimethyl-formamide at 20℃; for 20h;	216.3 Step 3 EXAMPLE 216; To a solution of Example 218 (20.0 mg, 0.09 mmol) in anhydrous DMF (0.2 ml) was added NaH (5.4 mg, 0.14 mmol) at 0° C. under nitrogen atmosphere, after 2 min, the reaction mixture was further treated with 3-bromopentane (0.12 ml, 0.9 mmol) and resulting reaction solution was stirred at rt for 20 h. The mixture was diluted with water (2.0 ml) and extracted with methylene chloride (3×2 ml). The combined extracts was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The solid was purified by reverse-phase preparative HPLC and the fraction containing the product was concentrated in vacuo and diluted with 1.0 N aqueous hydrochloric acid (1-2 ml), and lyophilized to yield 8.0 mg (17%) of the titled compound as a yellow solid. HPLC Ret. time: 4.65 min. LCMS MH+ (m/z)=489.21. 1H NMR: (CDCl3, 400 MHz): δ 9.69 (d, 1H), 8.71 (d, 1H), 8.60 (d, 1H), 7.84 (s, 1H), 7.32 (s, 1H), 6.60 (s, 2H), 5.78 (brs, 1H), 4.09 (m, 1H), 3.29 (m, 2H), 2.08 (s, 6H), 1.71 (m, 2H), 1.62 (m, 4H), 0.98 (t, 3H), 0.90 (t, 6H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2006/178388, 2006, A1 Location in patent: Page/Page column 120

15
[ 1809-10-5 ]
[ 211244-81-4 ]
[ 211245-36-2 ]

Yield	Reaction Conditions	Operation in experiment
348 mg (50%)	With NaH; In N-methyl-acetamide; ethyl acetate; mineral oil;	Example 75 8-Isopentyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> To a suspension of NaH (150 mg of a 60% suspension of NaH in mineral oil) in 10 mL of dimethylformamide was added <strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> (508 mg, 2.63 mmol). The reaction mixture was heated to 50 C. resulting in an orange solution. The solution was cooled slightly, and 3-bromopentane (500 muL, 3.97 mmol) was added. The reaction was heated at 50 C. for 1 hour, then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography eluding with a gradient of 1:3 ethyl acetate:hexane to all ethyl acetate to provide 348 mg (50%) of 8-isopentyl-<strong>[211244-81-4]2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong>, as an oil.

Reference： [1]Patent: US2004/224958,2004,A1

16
triazolone [ No CAS ]
[ 1809-10-5 ]
1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole [ No CAS ]
[ 210562-85-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With lithium perchlorate; caesium carbonate In N,N-dimethyl-formamide; acetonitrile	36 (2R,3R)-2-(2,4-Difluorophenyl)-3-[4-{4-[2-(3-pentyl)-2H-1,2,4-triazol-3-one-4-yl]-1-yl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol. Example 36 (2R,3R)-2-(2,4-Difluorophenyl)-3-[4-{4-[2-(3-pentyl)-2H-1,2,4-triazol-3-one-4-yl]-1-yl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol. To a mixture of triazolone 35 (248 mg, 0.5 mmol) and cesium carbonate (326 mg, 1 mmol) in DMF, 3-bromopentane (226 mg, 1.5 mmol) was added. The reaction mixture was heated at 80° C. for 18 h and concentrated in vacuo. The residue was treated with crushed ice, extracted with ethyl acetate (3*30 ml). The combined extract was washed with brine, dried (Na2 SO4) and the solvent was removed under rduced pressure. The resulting crude product was purified on a column of silica gel (hexane/EtOAc) to give the title compound 36 as a crystaline solid (240 mg, 85%). The title compound was also prepared in an alternate method in a convergent approach according to Scheme-1. Thus a mixture of (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane IV, piperazino compound XXIII (R=3-pentyl) and lithium perchlorate were heated in acetonitrile for 48 h. After usual workup and chromatographic purification, the title compound was obtained in 75% yield. m.p.: 143-145° C. 1 H NMR (CDCl3)δ: 0.88 (t, 6H, 2XCH3), 0.98 (d, 3H, CH3), 1.65-1.8 (m, 4H, 2XCH2), 2.60 (m, 2H, CH2), 3.1 (m, 3H, CH2 and CH), 3.2 (m, 4H, 2XCH2), 4.12 (m, 1H, CH), 4.9 (AB q, 2H, CH2), 5.18 (s, 1H, OH), 6.7-6.8 (m, 2H, Ar--H), 6.97 (d, 2H, Ar--H, J=9 Hz), 7.4-7.6 (d and m merged, 3H, Ar--H), 7.64 (s, 1H, Het-H), 7.79 (s, 1H, Het-H), 7.96 (s, 1H, Het-H). FAB-MS: 567.3 (MH+), calcd. C29 H36 F2 N8 O2 566.657.
	With lithium perchlorate; caesium carbonate In N,N-dimethyl-formamide; acetonitrile	36 (2R,3R)-2-(2,4-Difluorophenyl)-3-[4-{4-[2-(3-pentyl)-2H-1,2,4-triazol-3-one-4-yl]-1-yl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol. Example 36 (2R,3R)-2-(2,4-Difluorophenyl)-3-[4-{4-[2-(3-pentyl)-2H-1,2,4-triazol-3-one-4-yl]-1-yl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol. To a mixture of triazolone 35 (248 mg, 0.5 mmol) and cesium carbonate (326 mg, 1 mmol) in DMF, 3-bromopentane (226 mg, 1.5 mmol) was added. The reaction mixture was heated at 80 °C for 18 h and concentrated in vacuo. The residue was treated with crushed ice, extracted with ethyl acetate (3 X 30 ml). The combined extract was washed with brine, dried (Na2SO4) and the solvent was removed under rduced pressure. The resulting crude product was purified on a column of silica gel (hexane/EtOAc) to give the title compound36 as a crystaline solid (240 mg, 85%). The title compound was also prepared in an alternate method in a convergent approach according to Scheme-1. Thus a mixture of (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-(1 H-1,2,4-triazol-1-yl)methyloxirane IV, piperazino compound XXIII (R= 3-pentyl) and lithium perchlorate were heated in acetonitrile for 48 h. After usual workup and chromatographic purification, the title compound was obtained in 75% yield. m.p.: 143-145 °C. 1H NMR (CDCl3)δ: 0.88 (t, 6H, 2XCH3), 0.98 (d, 3H, CH3), 1.65-1.8 (m, 4H, 2XCH2), 2.60 (m, 2H, CH2), 3.1 (m, 3H, CH2 and CH), 3.2 (m, 4H, 2XCH2), 4.12 (m, 1H, CH), 4.9 (AB q, 2H, CH2), 5.18 (s, 1H, OH), 6.7-6.8 (m, 2H, Ar-H), 6.97 (d, 2H, Ar-H, J=9 Hz), 7.4-7.6 (d and m merged, 3H, Ar-H), 7.64 (s, 1H, Het-H), 7.79 (s, 1H, Het-H), 7.96 (s, 1H, Het-H). FAB-MS: 567.3 (MH+), calcd. C29H36F2N8O2 566.657.

Reference： [1]Current Patent Assignee: NAEJA PHARMACEUTICAL - US6153616, 2000, A
[2]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - EP889881, 2003, B1

17
[ 1809-10-5 ]
[ 211244-81-4 ]
[ 352359-84-3 ]

Yield	Reaction Conditions	Operation in experiment
44%		Example 276 8-(1-Ethyl-propyl)-<strong>[211244-81-4]2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> The title compound was prepared from <strong>[211244-81-4]2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one</strong> (10 g, 51.7 mmol) and 3-bromopentane (6.5 mL, 52 mmol) by using the procedure described in Example 272 (Yield 44%). MS (CI) 264.0 MH+.

Reference： [1]Patent: US2004/224958,2004,A1

18
[ 1809-10-5 ]
[ 82205-58-1 ]
[ 1029803-90-4 ]

Yield	Reaction Conditions	Operation in experiment
19%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 6h;	Reference Example 96: l-(l-Ethyl-propyl)-4-(5-nitro-pyridin-2-yI)-piperazine. To a solution of l-(5-nitro-pyridin-2-yl)-piperazine (2.2 g, 10.5 mmol) in DMF (10 mL) were added potassium carbonate (2.9 g, 21 mmol) and 3-bromopentane (4.8 g, 31.7 mmol). The mixture was heated at 120 C for six hours. DMF was removed in vacuo to give a residue which was partitioned between water and DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated to give 1-(1- ethyl-propyl)-4-(5-nitro-pyridin-2-yl)-piperazine (550 mg, 19%) as a yellow solid.

Reference： [1]Patent: WO2008/62182,2008,A1 .Location in patent: Page/Page column 135

19
[ 1809-10-5 ]
[ 81386-86-9 ]
[ 1040738-94-0 ]

Yield	Reaction Conditions	Operation in experiment
48%	With cesium fluoride In N,N-dimethyl-formamide at 20℃;	Y To a mixture of D-1 (108 mg, 0.40 mmol) and CsF (182 mg, 1.2 mmol) in DMF (2 mL) was added 3-Bromo-pentane (91 mg, 0.60 mmol). The reaction mixture was stirred at room temperature for overnight. Chromatograph on silica gel (10:1 hexane/EtOAc) gave 66 mg (48%) of F-25 as colorless oil. 1H NMR (300 MHz, CDCl3) δ7.30-7.16 (m, 5H), 7.12 (d, J=8.0 Hz, 2H), 6.79 (d, J=8.0 Hz, 2H), 4.48 (t, J=9.0 Hz, 1H), 4.06-3.99 (m, 3H), 3.01 (d, J=9.0 Hz, 2H), 1.71-1.58 (m, 4H), 1.10 (t, J=7.5 Hz, 3H), 0.92 (t, J=7.5 Hz, 6H); MS (ES) m/z: 363 (M+Na+).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2008/176912, 2008, A1 Location in patent: Page/Page column 29

20
[ 1809-10-5 ]
[ 91925-82-5 ]
[ 955887-39-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1663 - 1667

21
[ 1809-10-5 ]
[ 123-08-0 ]
[ 1186634-28-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate In N,N-dimethyl-formamide at 20 - 60℃;	19.1 To a stirred solution of 4-hydroxybenzaldehyde (1 g, 8.19 mmol) in N, N- dimethylformamide (15 ml) at room temperature was added potassium carbonate (2.26 g,16.39 mmol) and 3-bromopentane (1.2 gm, 9.00 mmol). The reaction mixture was heated to60 0C for 8 h . The reaction mixture was cooled to room temperature.The reaction mixture was poured into cold water (40 ml). The organic material was extracted in ethyl acetate (2x 25 ml). The combined organic layer was washed with water (30 ml) and brine (25 ml), dried over anhydrous sodium sulfate and concentrated under vacuo to afford colorless oil (1.5 g, 96 %).
96%	With potassium carbonate In N,N-dimethyl-formamide at 20 - 60℃;	11.1 To a stirred solution of 4-hydroxybenzaldehyde (1 g, 8.19 mmol) in N, N- dimethylformamide (40 ml) at room temperature was added potassium carbonate (2.26 g, 16.39 mmol) and 3-bromopentane (1.2 gm, 9.00 mmol). The reaction mixture was heated at 60 0C for 8 h. The reaction mixture was cooled to room temperature. The reaction mixture was poured into cold water (40 ml). It was extracted in ethyl acetate (2x 25 ml). The combined organic layer was washed with water (30 ml) and brine (25 ml), dried over anhydrous sodium sulfate and concentrated under vacuo to afford colorless oil (1.5 g , 96 %).
78%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 12h; Inert atmosphere; Heating;

With potassium carbonate In N,N-dimethyl-formamide at 50 - 100℃;

8.1 Step 1: Step 1: (0054) A mixture of 4-hydroxybenzaldehyde (12.2 g, 100 mmol, 1 eq), 3-bromopentane (0.81.5 eq) and potassium carbonate (1-3 eq) was added with 30 ml of DMF, and stirred at 50100t for 516 hours, wherein TLC (PE:EA=5:1) gave a new spot with low polarity, and showed that a little amount of 4-hydroxybenzaldehyde had not been reacted. The resulting solution was cooled to room temperature, and then added with 100 ml of dichloromethane and 100 ml of water, and the layers were separated. The resulting organic phase was washed with water twice, dried over about 20 g of anhydrous sodium sulfate for about 30 minutes, filtrated to remove the inorganic salt, and subjected to a gradient elution from 100% petroleum ether to petroleum ether/ ethyl acetate (5:1) over a 200300 mesh silica gel column to give pure 4-(3-pentoxy)benzaldehyde.

Reference： [1]Current Patent Assignee: LUPIN LIMITED - WO2009/109998, 2009, A1 Location in patent: Page/Page column 48
[2]Current Patent Assignee: LUPIN LIMITED - WO2009/109999, 2009, A1 Location in patent: Page/Page column 61
[3]Zhang, Jian; Murugan, Natarajan Arul; Tian, Ye; Bertagnin, Chiara; Fang, Zengjun; Kang, Dongwei; Kong, Xiujie; Jia, Haiyong; Sun, Zhuosen; Jia, Ruifang; Gao, Ping; Poongavanam, Vasanthanathan; Loregian, Arianna; Xu, Wenfang; Ma, Xiuli; Ding, Xiao; Huang, Bing; Zhan, Peng; Liu, Xinyong [Journal of Medicinal Chemistry, 2018, vol. 61, # 22, p. 9976 - 9999]
[4]Current Patent Assignee: GUANGZHOU INSIGHTER BIOTECHNOLOGY CO LTD - US2016/340299, 2016, A1 Location in patent: Paragraph 0053; 0054

22
[ 256411-39-9 ]
[ 1809-10-5 ]
[ 713147-45-6 ]

Yield	Reaction Conditions	Operation in experiment
		The above nitrile (9.2 g, 41 mmol) was dissolved in dichloromethane (50 mL) and trifluoroacetic acid (15 mL) was added. The mixture was stirred for 45 min at ambient temperature and then the solvent was evaporated. The residue was dissolved in acetonitrile (200 mL) and with stirring, excess potassium carbonate was added. The mixture was filtered and the solvent was evaporated. The oily residue was dissolved in acetonitrile (150 mL) and 3-pentylbromide (15.6 g, 105 mmol) and potassium carbonate (25.5 g, 185 mmol) were added and the reaction mixture was stirred at reflux temperature overnight. The mixture was allowed to cool, then filtered and the solvent evaporated. The residue was dissolved in ethyl acetate (200 mL) and the organic phase was washed with water (20 mL). The organic phase was dried (MgSO4) in the presence of activated carbon, filtered and the solvent was evaporated. This afforded 7.8 g of crude 2-(1-(1-ethylpropyl)piperidin-4-yl)acetonitrile

Reference： [1]Patent: US2005/107434,2005,A1 .Location in patent: Page/Page column 17-18

23
[ 1809-10-5 ]
[ 1268712-97-5 ]
[ 1268709-63-2 ]

Yield	Reaction Conditions	Operation in experiment
17%	With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 12h;	15 Example 15: 7V-cyclopentyl-l-(5,6-dichloro-l-(pentan-3-yl)-lH-benzo[d]imidazol-2- yl)piperidine-4-carboxamideTo a solution of Λ/-cyclopentyl-l-(5,6-dichloro-lH-benzo[d]imidazol-2-yl)piperidine-4- carboxamide (0.10 g, 0.26 mmol) in N,Λ/-dimethylformamide (0.5 mL) caesium carbonate (0.33g, 1 mmol) and [l,l'-bis(diphenylphosphino)ferrocene] dichloropalladium(II) (PdCl2(dppf), 1.0 mg, 0.0026 mmol) were added, followed by 3-bromopentane (59 mg, 0.39 mmol). The reaction mixture was heated at 12O0C for 12 hours, concentrated in vacuo and the residue extracted with ethyl acetate (2 x15 mL). The combined organic phases were washed with water (3 x 15 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was subjected to column chromatography (silica gel) to give 10 mg (17%) of N-cyclopentyl-l-(5,6- dichloro- 1 -(pentan-3-yl)- lH-benzo[d]imidazol-2-yl)piperidine-4-carboxamide. LC-MS (m/z) 451.3 (M+l).

Reference： [1]Current Patent Assignee: KAROLINSKA DEVELOPMENT AB - WO2011/23812, 2011, A1 Location in patent: Page/Page column 72

24
[ 1809-10-5 ]
[ 3034-38-6 ]
[ 865774-08-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2631 - 2636

25
[ 1809-10-5 ]
[ 1338727-93-7 ]
[ 1338728-00-9 ]

Yield	Reaction Conditions	Operation in experiment
15%	With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide; mineral oil at 20 - 80℃; for 24.5h; Inert atmosphere;	5.1.55. 3-(2-Chloro-4-methoxyphenyl)-N-(1-ethylpropyl)-2-methyl-6,7-dihydrofuro[2,3-d]pyrazolo[1,5-a]pyrimidin-8-amine (31) To a stirred solution of 44 (200 mg, 0.60 mmol) in DMF (3.0 mL) was added NaH (26 mg, 0.67 mmol , 60% in mineral oil) and tetrabutylammoniun iodide (catalytic amount) at ambient temperature under argon atmosphere. After 1.5 h, the reaction mixture was allowed to be heated at 50 °C for 1 h, then at 80 °C for 22 h. The reaction mixture was cooled to ambient temperature and diluted with hexane/EtOAc (1:1). The organic layer was washed with brine and dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using Et2O/hexane (1:2-1:3) to give 31 (36 mg, 15% yield) as an ivory powder. TLC Rf = 0.67 (EtOAc/hexane, 1:1) ; MS (APCI, Pos) m/z 401 (M+H)+ ; FABHRMS calcd for C21H26ClN4O2: 401.1744. Found: 401.1743; 1H NMR (300 MHz, CDCl3) δ 7.26 (m, 1H), 7.01 (d, J = 2.6 Hz, 1H), 6.84 (dd, J = 8.5, 2.6 Hz, 1H), 6.18 (d, J = 10.8 Hz, 1H), 4.62 (m, 2H), 3.81 (s, 3H), 3.60 (m, 1H), 3.34 (t, J = 8.2 Hz, 2H), 2.30 (s, 3H), 1.68 (m, 4H), 1.01 (m, 6H); mp 139-141 °C.

Reference： [1]Location in patent: experimental part Saito, Tetsuji; Obitsu, Tetsuo; Kondo, Takashi; Matsui, Toshiaki; Nagao, Yuuki; Kusumi, Kensuke; Matsumura, Naoya; Ueno, Sonoko; Kishi, Akihiro; Katsumata, Seishi; Kagamiishi, Yoshifumi; Nakai, Hisao; Toda, Masaaki [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5432 - 5445]

26
[ 1809-10-5 ]
[ 1338362-99-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-bromopentane With magnesium In diethyl ether at 0℃; Stage #2: With nitrogen trifluoride In diethyl ether at -25℃; for 1h; Inert atmosphere;	4.2. General procedure for the synthesis of N,N-difluoroanimoalkanes 5 g of magnesium turnings were suspended with stirring in 200 ml diethyl ether at 0 °C. The requisite haloalkane (0.2 mol) was added dropwise. The reaction was stirred a further 1-2 h. Stirring was ceased and the solution allowed to settle. The clear solution was transferred via non-metallic cannula to a 250 ml pressure-rated glass round bottomed flask and held at 0 °C.A 500 ml pressure-rated glass round bottomed flask, with Teflon coated magnetic stir bar was charged with 200 ml diethyl ether. This solution was cooled to 0 °C and sparged with NF3. The solution was cooled to -25 °C and pressurized with NF3 to 140 psi.The Grignard solution in the 250 ml flask was slowly transferred under pressure of N2 to the NF3 solution in the 500 ml flask. The transfer cannula was non-metallic and positioned with the outlet end below the surface of the NF3 solution. The solution was stirred 1 hour, then vented and quenched with sat. aq. NH4Cl solution. After warming to room temperature, the phases were separated. The ether layer was dried with MgSO4 and filtered. Excess ether was removed by fractional distillation through a glass ring packed column at ∼18 °C under slight vacuum (400 mmHg). The difluoroaminoalkane product was isolated in various fractions at about 20 °C (∼1 mmHg) without concern for yield. The purest fraction as per GC was analyzed by NMR.

Reference： [1]Location in patent: experimental part Belter, Randolph K. [Journal of Fluorine Chemistry, 2012, vol. 137, p. 73 - 76]

27
[ 1809-10-5 ]
[ 1400703-87-8 ]
[ 1400705-21-6 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃;	II.141 A mixture of (S)-2-({2-[3-(lH-indazol-4-yl)-propylamino]-4,6-dimethyl-pyrimidine-5-carbon- yl}-amino)-3-[(thiophene-2-carbonyl)-amino]-propionic acid (0.05g, 0.095mmol), 3-bromopentane (0.022g, 0.143mmol), and potassium carbonate (0.020g, 0.143mmol) in DMF (1ml) was stirred at rt overnight. 3-bromopentane (0.022g, 0.143mmol), and potassium carbonate (0.020g, 0.143mmol) were added and the reaction mixture was stirred at 50°C for 5 h, then cooled to rt and stirred for 2 days. The mixture was diluted with EtOAc, washed with brine, dried over Na2S04, filtered, concentrated in the presence of silica gel and chromatographed (50-100% EtOAc in hexane) to give the title compound (28.3mg, 50% yield). MS m/e 592.2 (M+H+).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2012/123467, 2012, A1 Location in patent: Page/Page column 125

28
[ 1809-10-5 ]
[ 1160059-83-5 ]
[ 1426254-13-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium hydride In N,N-dimethyl-formamide	5.2. General procedure for the preparation of 7-alkoxyl-β-carboline derivatives General procedure: A mixture of 7-hydroxyl-β-carbolines 3a-d (5 mmol) and anhydrous DMF (50 ml) was stirred at room temperature until clear, and then 60% NaH (0.3 g, 7.5 mmol) and alkyl halogenide (15 mmol) were added. The mixture was stirred at room temperature for 0.5-2 h. After completion of the reaction as indicated by TLC, the solution was poured into H2O (150 ml), and extracted with ethyl acetate. The organic phase was made acidic with concentrated hydrochloric acid. Upon removal of solvent, the residue was crystallized from acetone to afford yellow solid. The solid was dissolved in water and made basic with sodium bicarbonate, and the aqueous mixture extracted with ethyl acetate. The organic phase was washed with water and brine, then dried over anhydrous sodium sulfate, filtered and evaporated. The resulting oil was crystallized from ethyl ether or ethyl ether-petroleum ether.

Reference： [1]Cao, Rihui; Fan, Wenxi; Guo, Liang; Ma, Qin; Zhang, Guoxian; Li, Jianru; Chen, Xuemei; Ren, Zhenghua; Qiu, Liqin [European Journal of Medicinal Chemistry, 2013, vol. 60, p. 135 - 143]

29
[ 1809-10-5 ]
[ 1015792-02-5 ]
[ 1015792-06-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium hydride In N,N-dimethyl-formamide	5.2. General procedure for the preparation of 7-alkoxyl-β-carboline derivatives General procedure: A mixture of 7-hydroxyl-β-carbolines 3a-d (5 mmol) and anhydrous DMF (50 ml) was stirred at room temperature until clear, and then 60% NaH (0.3 g, 7.5 mmol) and alkyl halogenide (15 mmol) were added. The mixture was stirred at room temperature for 0.5-2 h. After completion of the reaction as indicated by TLC, the solution was poured into H2O (150 ml), and extracted with ethyl acetate. The organic phase was made acidic with concentrated hydrochloric acid. Upon removal of solvent, the residue was crystallized from acetone to afford yellow solid. The solid was dissolved in water and made basic with sodium bicarbonate, and the aqueous mixture extracted with ethyl acetate. The organic phase was washed with water and brine, then dried over anhydrous sodium sulfate, filtered and evaporated. The resulting oil was crystallized from ethyl ether or ethyl ether-petroleum ether.

Reference： [1]Cao, Rihui; Fan, Wenxi; Guo, Liang; Ma, Qin; Zhang, Guoxian; Li, Jianru; Chen, Xuemei; Ren, Zhenghua; Qiu, Liqin [European Journal of Medicinal Chemistry, 2013, vol. 60, p. 135 - 143]

30
[ 1809-10-5 ]
(E)-4-methoxy-N-(1-phenylethylidene)benzenamine [ No CAS ]
[ 1443686-11-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 3-bromopentane; (E)-4-methoxy-N-(1-phenylethylidene)benzenamine With neopentylmagnesium bromide; cobalt(II) bromide; 1,3-Diisopropyl-4,5-dihydro-3H-imidazol-1-ium tetrafluoroborate In tetrahydrofuran at 0 - 20℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran Schlenk technique; Inert atmosphere;
63%	With 1,3-diisopropylimidazolium tetrafluoroborate; neopentylmagnesium bromide; cobalt(II) bromide In tetrahydrofuran at 20℃; for 24h; Schlenk technique;	3ax General procedure: A 10 mL Schlenk tube was charged with CoBr2 (6.6 mg, 0.03mmol), 1,3-diisopropyl-1H-benzimidazol-3-ium bromide (L4; 8.5mg, 0.03 mmol), 4-methoxy-N-[(1E)-1-phenylethylidene]aniline(1a, 67.6 mg, 0.30 mmol), 1-chlorooctane (2a, 76.5 μL, 0.45 mmol), and THF (0.69 mL). A 1.92 M solution of t-BuCH2MgBr inTHF (0.31 mL, 0.60 mmol) was added dropwise at 0 °C, and themixture was stirred at r.t. for 6 h. The reaction was quenched by theaddition of 3 M aq HCl (1.0 mL), and the mixture was stirred at r.t.for 1 h, then extracted with EtOAc (3 × 10 mL). The organic layerswere combined, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by chromatography [silicagel, hexane-EtOAc (40:1)].

Reference： [1]Gao, Ke; Yoshikai, Naohiko [Journal of the American Chemical Society, 2013, vol. 135, # 25, p. 9279 - 9282]
[2]Gao, Ke; Yamakawa, Takeshi; Yoshikai, Naohiko [Synthesis, 2014, vol. 46, # 15, p. 2024 - 2039]

31
[ 6332-56-5 ]
[ 1809-10-5 ]
[ 749265-10-9 ]
[ 1614217-56-9 ]

Yield	Reaction Conditions	Operation in experiment
11.6%; 25%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 3h;	PreparationA. 1: Synthesis of 3-nitro-1-(pentan-3-yl)pyridin-2(1H)-one: To a solution of 3-nitropvridin-2-ol (4g. 0.O28mols, combi blocks) in DMF (15m1) was added K2C03 (1 1 .2g, 0.084 mol) followed by 3-bromo pentane (6.4g, 0.042mo1, Aldrich). The reaction was heated to I 00CC for 3h. The reaction mixture was cooled to room temperature and dilutedwith Ice cold water. The product was extracted with EtOAc (5 x 50 mL), The combined organic layers was successively washed with water (2x25m1), brine (2x25rn1) and dried over sodium sulphate. The organic layer was concentrated under reduced pressure. The crude material was purified by silica gel (60-120) column chromatography by eluting with 05-10% EtOAc in hexane. First eluting compound was identified as 3-nitro-2-(pentan-3-vloxy)pyridine 0.7g,(ll.6%) ?H NMR (400 MHz. DMSO-do): oe 8.46 (dd, .1=2.4Hz, 1 H) 8.38 (dd, J =6.4Hz, 1 H) 7.19 (d, .1 =4.8Hz,IH), 5,25 (m,IH), 1.7 (m.4H), 0.89 (t, J81-Iz, 6Hz) MS mlz 211 (M+H+), The second eluting compound containing the product was collected and evaporated to dryness to afford 3- nitro-1-(pentan-3-vl)pvridin-2(IH)-one 1 5g, ( 25%) as yellowish liquid. ?H NMR (400 MHz, DMSO-do): 8.29(dd, J2Hz, IH), 7.57 (dd, J=2.4Flz, 1H), 6.36 (t, J7.6Hz, IH), 5.06 (bs,IH), 1.92(m, 2H), 1.88 (m, 2H) 0.89 (t ,J7,6Hz, 6H), Ms m/z: 211 (M+H).

Reference： [1]Patent: WO2014/91265,2014,A1 .Location in patent: Page/Page column 21; 22

32
[ 1809-10-5 ]
[ 10111-08-7 ]
1-(pentan-3-yl)-1H-imidazole-2-carbaldehyde [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 4713 - 4726

33
[ 2295-31-0 ]
[ 1809-10-5 ]
3-(pentan-3-yl)thiazolidine-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: thiazoline-2,4-dione With potassium hydroxide In ethanol for 0.5h; Reflux; Stage #2: 3-bromopentane In N,N-dimethyl-formamide Reflux;	2.1 General procedure A: synthesis of thiazolidine-2,4-dione potassium salt (2) and 3-alkylthiazolidine-2,4-diones (3) with exemplary compound data General procedure: The compounds were prepared according to the procedure previouslydescribed.19,30 To a refluxing solution of thiazolidine-2,4-dione (43 mmol) in ethanol (25 mL) was added a hot solutionof potassium hydroxide (45 mmol) in ethanol (25 mL). After additionalrefluxing for 30 min, the mixture was cooled to room temperatureand the precipitate was filtered and washed with coldethanol. The obtained potassium 2,4-dioxothiazolidin-3-ide (2)(5 mmol) was refluxed with alkyl halides (5.5 mmol) in DMF(15 mL) for 3-4 h. After cooling to room temperature and additionof water (50 mL), the crude product was extracted 3 times withethyl acetate, washed with brine, and purified by flash chromatography(cyclohexane/ethyl acetate).

Reference： [1]Bastos Lima, Allan; Behnam, Mira A.M.; El Sherif, Yasmin; Nitsche, Christoph; Vechi, Sergio M.; Klein, Christian D. [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5748 - 5755]

34
[ 1809-10-5 ]
[ 201733-56-4 ]
5,5-dimethyl-2-(pentan-3-yl)-1,3,2-dioxaborinane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With triphenylphosphine; copper(I) bromide; lithium tert-butoxide In N,N-dimethyl acetamide at 25℃; for 18h; Inert atmosphere; Schlenk technique;	Experimental Procedure C for Examples Described in Table 3 General procedure: In air, CuBr (7.1 mg, 0.05 mmol), PPh3 (17.03 mg, 0.065 mmol), LiOtBu(80 mg, 1mmol), and bis(neopentyl glycolato) diboron (168mg, 0.75 mmol ) were added to aSchlenk tube equipped with a stir bar. The vessel was evacuated and filled with argon(three cycles). DMAc (1 mL), alkyl halide (0.5 mmol) were added in turn by syringeunder an argon atmosphere (if the alkyl halide is a solid, it was added along with theCuBr). The resulting reaction mixture was stirred vigorously at 25 °C for 18 h. Thereaction mixture was then diluted with EtOAc, filtered through silica gel with copiouswashings (petroleum ether to EtOAc), concentrated, and purified by columnchromatography.

Reference： [1]Lou, Xin; Zhang, Zhen-Qi; Liu, Jing-Hui; Lu, Xiao-Yu [Chemistry Letters, 2016, vol. 45, # 2, p. 200 - 202]

35
[ 269410-08-4 ]
[ 1809-10-5 ]
1-(pentan-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.78%	With caesium carbonate In N,N-dimethyl-formamide at 100℃; Sealed tube;	4 Preparation 41 -(pentan-3 -yl)-4-(4,4,5 .5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-pyrazole 1003481 4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-pyrazole (4.0 g, 20.61 mmol), 3-bromopentane (5.121 mL, 41.23 mmol) and Cs2CO3 (8.060 g, 24.74 mmol) were suspended in DMF (8 mL) and sealed in a glass pressure vessel and heated to 100 °C overnight. After cooling to ambient temperature, the cap was removed slowly [pressure releasej, partitioned between water (20 mL) and EtOAc (100 mL), washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified over silica gel (15% EtOAc in hexanes) to afford 1 -(pentan-3 -yl)-4-(4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrazole (3.8 g, 14.38 mmol, 69.78 % yield) as a clear colorless oil.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; PFIZER INC - WO2016/90285, 2016, A1 Location in patent: Paragraph 00348

36
[ 1809-10-5 ]
[ 885518-49-0 ]
methyl 6-bromo-1-(pentan-3-yl)-1H-indazole-4-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 7617 - 7633

37
[ 1809-10-5 ]
[ 57606-65-2 ]
[ 28593-13-7 ]
C₁₁H₁₅F [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 14793 - 14797
Angew. Chem.,2016,vol. 128,p. 15013 - 15017,5

38
[ 1809-10-5 ]
[ 66107-34-4 ]
[ 1595-07-9 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 14793 - 14797
Angew. Chem.,2016,vol. 128,p. 15013 - 15017,5

39
[ 1809-10-5 ]
[ 66107-36-6 ]
[ 87170-05-6 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 14793 - 14797
Angew. Chem.,2016,vol. 128,p. 15013 - 15017,5

40
[ 65007-00-3 ]
[ 1809-10-5 ]
[ 7399-50-0 ]
[ 2294-76-0 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 14793 - 14797
Angew. Chem.,2016,vol. 128,p. 15013 - 15017,5

41
[ 1809-10-5 ]
[ 78818-15-2 ]
benzyl 4-pentyl 3‘-yl-3-oxopiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.7%		To a solution of compound I-16 (1.1 g, 4.7 mmol) in DMF (25 mL), NaH (282 mg, 7.05 mmol)was added and the mixture was stirred under argon at room temperature for 1 h and then the3-bromopentane (1.16 mL, 9.4 mmol) was added and the reaction mixture was stirred under argonat 40 for 48 h. H2O was added to quench the reaction. Then ethyl acetate (80 mL) was added tothe solution and then the organic layer was washed with brine (30 mL × 2) and then was driedover anhydrous MgSO4. After filtration and concentration, the crude product I-17 was obtainedand purified with column chromatography (petroleum ether/ethyl acetate = 2:1 to methylenechloride /methanol = 20:1) to give compound I-17 as white oil (850 mg, 60.7%).
55.7%		N-benzyloxycarbonyl-3-oxobutazine (40011 ^, 1.7111111101) was added to a three-necked flask,Add about 101 ^ anhydrous DMF, nitrogen under the protection of NaH (102mg, 2.56mmo 1), continue to stir for 60min, by adding 3-bromopentane, room temperature reaction overnight. The solvent was evaporated under reduced pressure, and the aqueous solution was concentrated twice and the organic layer was concentrated. The column was chromatographed to give 263 mg of an oil in 55.7% yield.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 132,p. 26 - 41
[2]Patent: CN107098886,2017,A .Location in patent: Paragraph 0206; 0207

42
[ 1809-10-5 ]
[ 182223-54-7 ]
benzyl (1-(pentan-3-yl)piperidin-4-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
220 mg	With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 5h;Reflux;	General procedure: To a solution of compound I-7 (900 mg, 2.62 mmol) in DCM (30 mL), TFA (4.5 mL, 52.32 mmol)was added and then the reaction mixture was stirred at room temperature for 1 h and then was evaporated to give the crude product used in the next step. The mixture of the amine, DIEA (3.6mL, 20.93 mmol) and 1-bromo-3-methylbut-2-ene (1.5 mL, 13.08 mmol) in acetonitrile washeaded to reflux for 5 h and then was evaporated. Then ethyl acetate (60 mL) was added to thesolution and then the organic layer was washed with brine (20 mL × 2) and then was dried overanhydrous MgSO4. After filtration and concentration, the crude product I-8b was obtained andpurified with column chromatography (methylene chloride /methanol = 40:1 to 25:1) to givecompound I-8b light yellow oil (350 mg, 49.3%).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 132,p. 26 - 41

43
[ 78646-39-6 ]
[ 1809-10-5 ]
2-(4-methoxy-3-(pentan-3-yl)phenoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With [RhCl₂(p-cymene)]2; potassium carbonate; (adamant-1-yl)-acetic acid In benzene at 120℃; for 24h; Sealed tube; Inert atmosphere;
81%	With [RhCl₂(p-cymene)]2; potassium carbonate In benzene at 120℃; for 24h; Inert atmosphere;	2 Example 2: In a 20 mL pressure-resistant reaction tube, 40 mg (0.2 mmol) of 2- (4-methoxyphenoxy) pyridine was added,90 mg (0.6 mmol) of 3-bromopentane, 6 mg (0.01 mmol) of dichlorobis (4-methylisopropylphenyl)55 mg (0.4 mmol) of potassium carbonate, 11 mg (0.06 mmol) of 1-adamantane acid, 1.5 mL of benzene,Sealed under nitrogen, heated to 120° C reaction, stirred for 24 hours, after the reaction, the column chromatography,The desired product 2- (3-pentyl-4-methoxyphenoxy) pyridine 44mg, the yield was 81%.

Reference： [1]Li, Gang; Gao, Panpan; Lv, Xulu; Qu, Chen; Yan, Qingkai; Wang, Ya; Yang, Suling; Wang, Junjie [Organic Letters, 2017, vol. 19, # 10, p. 2682 - 2685]
[2]Current Patent Assignee: ANYANG NORMAL UNIVERSITY - CN107089940, 2017, A Location in patent: Paragraph 0008

44
[ 51933-81-4 ]
[ 1809-10-5 ]
5-methyl-2-(3-(pentan-3-yl)phenoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With [RhCl₂(p-cymene)]2; potassium carbonate; (adamant-1-yl)-acetic acid In benzene at 120℃; for 24h; Sealed tube; Inert atmosphere;
46%	With potassium carbonate In benzene at 120℃; for 24h; Inert atmosphere;	5 Example 5: In a 20 mL pressure-resistant reaction tube were placed 37 mg (0.2 mmol) of 5-methyl-2-phenoxypyridine,98 mg (0.6 mmol) 2-bromopentane, 55 mg (0.4 mmol) potassium carbonate,11 mg (0.06 mmol) of 1-adamantane acid, 1.5 mL of benzene, sealed under nitrogen, heated to 120° C ° C. to react,After stirring for 24 hours, the reaction mixture was separated by column chromatography to obtain 24 mg of the target product, 5-methyl-2- (2-pentylphenoxy) pyridine, in a yield of 46%.

Reference： [1]Li, Gang; Gao, Panpan; Lv, Xulu; Qu, Chen; Yan, Qingkai; Wang, Ya; Yang, Suling; Wang, Junjie [Organic Letters, 2017, vol. 19, # 10, p. 2682 - 2685]
[2]Current Patent Assignee: ANYANG NORMAL UNIVERSITY - CN107089940, 2017, A Location in patent: Paragraph 0011

45
[ 1809-10-5 ]
[ 4783-68-0 ]
2-(3-(3-pentyl)phenoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; adamantane-2-carboxylic acid; potassium carbonate; In benzene; at 120℃; for 24h;Inert atmosphere; Sealed tube;	To a 20 mL pressure-resistant reaction tube was added 34 mg (0.2 mmol) of <strong>[4783-68-0]2-phenoxypyridine</strong>, 90 mg (0.6 mmol) of 3-bromopentane,6 mg (0.01 mmol) of dichlorobis (4-methylisopropylphenyl) ruthenium,55 mg (0.4 mmol) of potassium carbonate, 11 mg (0.06 mmol) of 1-adamantanic acid, 1.5 mL of benzene,Under nitrogen conditions, heated to 120 C reaction, stirring for 24 hours, after the reaction, column chromatography,To give the desired product, 2- (3- (3-pentyl) phenoxy) 35 mg, in 73% yield.
73%	With [RhCl2(p-cymene)]2; potassium carbonate; In benzene; at 120℃; for 24h;Inert atmosphere;	34 mg (0.2 mmol) of <strong>[4783-68-0]2-phenoxypyridine</strong> was added to a 20 mL pressure-resistant reaction tube,90 mg (0.6 mmol) 3-bromopentane, 6 mg (0.01 mmol)Dichlorobis (4-methylisopropylphenyl) ruthenium,55 mg (0.4 mmol) of potassium carbonate, 11 mg (0.06 mmol) of 1-adamantane acid,1.5mL benzene, sealed under nitrogen, heated to 120 C reaction, stirred for 24 hours, after the reaction,Column chromatography afforded the desired product 2- (3- (3-pentyl) phenoxy) 35 mg, 73% yield.

Reference： [1]Organic Letters,2017,vol. 19,p. 2682 - 2685
[2]Patent: CN107032960,2017,A .Location in patent: Paragraph 0007
[3]Patent: CN107089940,2017,A .Location in patent: Paragraph 0007; 0014

46
[ 1809-10-5 ]
[ 4783-68-0 ]
[ 97218-43-4 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2682 - 2685
[2]Patent: CN107032960,2017,A

47
[ 1809-10-5 ]
[ 1227476-15-4 ]
3,3'-bis(3-pentyl)azobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate; Trimethylacetic acid In 1,4-dioxane at 120℃; for 24h; Inert atmosphere;	To a 20 mL pressure-resistant reaction tube was added 36 mg (0.2 mmol) of azobenzene,82 mg (0.6 mmol) of bromo-tert-butane,55 mg (0.4 mmol) of potassium carbonate,6 mg (0.06 mmol) of trimethylacetic acid,1.5 mL of 1,4-dioxane,Sealed under nitrogen conditions,Heated to 120 ° C reaction,Stirring for 24 hours,After the reaction, column chromatography was performed,The desired product, 3-tert-butylazobenzene, was 28 mg in 58% yield.The following table is a product synthesized using the technical scheme of the present invention and the corresponding yield:

Reference： [1]Current Patent Assignee: ANYANG NORMAL UNIVERSITY - CN106349102, 2017, A Location in patent: Paragraph 0010; 0011

48
[ 1809-10-5 ]
[ 1227476-15-4 ]
3-(3-pentyl)azobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate; Trimethylacetic acid In 1,4-dioxane at 120℃; for 24h; Inert atmosphere;	1 Example 1: To a 20 mL pressure-resistant reaction tube was added 36 mg (0.2 mmol) of azobenzene,90 mg (0.6 mmol) of 3-bromopentane,55 mg (0.4 mmol) of potassium carbonate, 6 mg (0.06 mmol) of trimethylacetic acid,1.5 mL of 1,4-dioxane, sealed under nitrogen conditions,Heated to 120 ° C reaction,Stirring for 24 hours,After the reaction, column chromatography was performed,The desired product, 3- (3-pentyl) azobenzene, was 38 mg in 76% yield.

Reference： [1]Current Patent Assignee: ANYANG NORMAL UNIVERSITY - CN106349102, 2017, A Location in patent: Paragraph 0007

49
[ 1809-10-5 ]
[ 501-60-0 ]
4,4'-dimethyl-3-(3-pentyl)azobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate; Trimethylacetic acid; In 1,4-dioxane; at 120℃; for 24h;Inert atmosphere;	To a 20 mL pressure-resistant reaction tube was added 42 mg (0.2 mmol) of 4,4'-dimethylazobenzene,90 mg (0.6 mmol) of 3-bromopentane,55 mg (0.4 mmol) of potassium carbonate,6 mg (0.06 mmol) of trimethylacetic acid, 1.5 mL of 1,4-dioxane,Sealed under nitrogen conditions,Heated to 120 C reaction,Stirring for 24 hours,After the reaction, column chromatography was performed,To give the desired product 4,4'-dimethyl 3- (3-pentyl) azobenzene as 34 mg in 60% yield.

Reference： [1]Patent: CN106349102,2017,A .Location in patent: Paragraph 0008

50
[ 1809-10-5 ]
4-(4-(4-(4-bromophenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one [ No CAS ]
4-(4-(4-(4-bromophenyl)piperazin-1-yl)phenyl)-2-(pentan-3-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.6%	With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere;	66 4-(4-(4-(4-bromophenyl)piperazin-1-yl)phenyl)-2-(pentan-3-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one (HB) To a stirred solution of compound FQ (300 nig, 0.75 mrnol) in DMF (10 mL) under argon atmosphere were added cesium carbonate (733 mg. 2.25 mmol) and 3-bromopentane (340 mg. 2.25 mmol) at 0 °C. The reaction mixture was warmed to RT and stirred for 16 h. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2 x 10 mL). The combined organic extracts were washed with water (10 mL), brine (30 mL), diied over anhydrous aaSOi and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluent: 30%EtOAc/Hexane) to afford compound HB (220 nig, 0.46 mmol, 62.6%) as an off-white solid. 1H NMR (500 MHz, DMSOi): δ 8.33 (s, 1H), 7.50 (cl, J = 9.0 Hz, 2H). 7.36 (d, J= 9.0 Hz. 2H), 7.09 (d, J= 9.0 Hz, 2H), 6.96 (d, J= 9.0 Hz, 2H), 3.89-3.86 (m, 1H), 3.91-3,76 (m. 4H), 3.34-3.24 (m, 4H), 1.73-1.58 (ni. 4H), 0.76 ( J = 7.4 Hz, 6H).

Reference： [1]Current Patent Assignee: NQP 1598 LTD - WO2017/117393, 2017, A1 Location in patent: Page/Page column 243

51
[ 35203-44-2 ]
[ 1809-10-5 ]
1-butyl-3-(3-pentyl)imidazolium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 80℃; for 48h;	The mixture of 1-butylimidazole and 3-pentylbromide was stirred at 80 C for two days.The crude product (yellowish oil) was extracted twice with diethyl ether, to remove unreacted components, evaporated and used without further purification for the anion exchange. 1H NMR (400 MHz; CDCl3) d (ppm) 0.84 (t, J = 7.34 Hz, 5 H) 0.93 (t, J = 7.46 Hz, 3 H)1.29?1.39 (m, 2 H) 1.79?2.00 (m, 6 H) 4.34?4.45 (m, 1 H) 4.38 (t, J = 7.34 Hz, 2 H) 7.40(tt, J = 1.83 Hz, 1 H) 7.53 (t, J = 1.83 Hz, 1 H) 10.57 (s, 1 H) 13C NMR (400 MHz; CDCl3) d (ppm) 10.42 (s) 13.55 (s) 19.49 (s) 28.23 (s) 32.28(s) 49.87 (s) 65.19 (s) 76.84 (s) 77.48 (s) 120.03 (s) 122.37 (s) 137.09 (s)MS 195.1857 (M?, cation), 78.9179, 80.9158 (M?, anion) (calculated C12H23N2195.1855 (cation), Br? 78,9189; 80,9168 (anion))FTIR(KBr) m = 3425, 3061, 2962, 2876, 1625, 1556, 1461, 1167, 878 cm1

Reference： [1]Journal of Solution Chemistry,2017,vol. 46,p. 1456 - 1474

52
[ 1809-10-5 ]
[ 59099-58-0 ]
[ 18272-73-6 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 1982 - 1986
Angew. Chem.,2018,vol. 130,p. 2000 - 2004,5

53
[ 1809-10-5 ]
[ 99724-19-3 ]
(1-(pentyl-3-yl)pyrrolidin-3-yl)carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 40℃; for 4h;	The compound 3-Boc-aminopyrrolidine (372 mg, 2 mmol),Add acetonitrile (15 mL),Add DIEA (0.52 mL, 3 mmol),Add 3-bromopentane (0.3 mL, 2.4 mmol),The reaction was heated to reflux. concentrate,Ethyl acetate (50 mL) was added and washed with a saturated NaCI solution (20 mL×2).Dry over anhydrous magnesium sulfate, column chromatography (MeOH: DCM = 1:40, MeOH: DCM = 1:30)Obtained a yellowish solid330mg,The yield was 64%.

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 3189 - 3202
[2]Patent: CN108727343,2018,A .Location in patent: Paragraph 0368; 0371; 0372

54
[ 3943-74-6 ]
[ 1809-10-5 ]
methyl 3-methoxy-4-(pentan-3-yloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With sodium hydride; sodium iodide In mineral oil at 65℃;
37%	With sodium hydride; sodium iodide In N,N-dimethyl-formamide; mineral oil at 65℃; for 4h;	methyl 4-(sec-butoxy)-3-methoxybenzoate General procedure: The title compound was synthesized by the method described previously with slight modifications151. To a DM F solution of methyl 4-hydroxy-3-methoxybenzoate (440 mg, 2.4 mmol, 1 equiv) was slowly added sodium hydride (60 % dispersion in mineral oil, 150 mg, 3.75 mmol, 1 .56 equiv) followed by 2-iodobutane (1 .4 mL, 12 mmol, 5 equiv). The solution was heated to 65°C and stirred 4 h. After cooling to rt, aqueous saturated LiCI was added and extracted with ethyl acetate. The organic layer was combined and washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography (Hexane: ethyl acetate = 5:1) gave the title compound as a white powder (200 mg, 35 %).1H NMR (500 MHz, CDCIs) δ 7.64 (dd, J = 8.5, 2.0 Hz, 1 H), 7.55 (d, J = 2.0 Hz, 1 H), 6.88 (d, J = 8.5 Hz, 1 H), 4.42 - 4.35 (m, 1 H), 3.90 - 3.88 (m, 6H), 1.89 - 1.77 (m, 1 H), 1.74 - 1.60 (m, 1 H), 1.35 (d, J = 6.1 Hz, 3H), 0.99 (t, J = 7.5 Hz, 3H).13C NMR (126 MHz, DMSO)5166.9, 151.9, 149.7, 123.4, 122.4, 113.4, 112.8, 76.5, 56.1, 51.9, 29.1, 19.2, 9.8.

Reference： [1]Kitamura, Seiya; Owensby, Anna; Wall, Daniel; Wolan, Dennis W. [Cell Chemical Biology, 2018, vol. 25, # 3, p. 301 - 12,308]
[2]Current Patent Assignee: SCRIPPS RESEARCH - WO2019/10165, 2019, A1 Location in patent: Page/Page column 36-38

55
[ 1809-10-5 ]
5-((1,3-dioxolan-2-yl)methyl)-5-(pyridin-2-yl)piperidin-2-one [ No CAS ]
5-((1,3-dioxolan-2-yl)methyl)-1-(pentan-3-yl)-5-(pyridin-2-yl)piperidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium <i>tert</i>-butylate In 1,2-dimethoxyethane at 60℃;	63.1 First step: 5-((1,3-dioxolan-2-yl)methyl)-1-(pentan-3-yl)-5-(pyridin-2-yl)piperidin-2- Ketone (63A) 5-((1,3-dioxolan-2-yl)methyl)-5-(pyridin-2-yl)piperidin-2-one (36D) at room temperature (0.7 g, 2.7 mmol) dissolved in ethylene glycol dimethyl ether(5mL), add uncle at room temperaturePotassium butoxide (0.3 g, 2.7 mmol), bromocyclopentane(0.4g, 2.7mmol), after adding, the temperature is raised to 60 degrees and the reaction is continued for 0.5h.Add to the reaction solution every 1h3-bromopentane (0.4 g, 2.7 mmol),Potassium tert-butoxide (0.3 g, 2.7 mmol) was added in an additional 8 times, and 20 mL of water was added to the reaction solution.Ethyl acetate extraction (20 ml × 2) was dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated under reduced pressure to remove the solvent.Column chromatography (methylene chloride / methanol = 30:1) gave the product as a yellow oil.5-((1,3-dioxolan-2-yl)methyl)-1-(pentan-3-yl)-5-(pyridin-2-yl)piperidin-2-one(63A) (0.7g, 86%).

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN109206417, 2019, A Location in patent: Paragraph 2248; 2252-2257

56
[ 1809-10-5 ]
[ 13466-38-1 ]
5-bromo-1-(pentan-3-yl)pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.5%	With caesium carbonate In 1,2-dimethoxyethane at 80℃; for 2h;	d Step d: Dissolve 5-bromo-2(1H)-pyridone (1.159mg, 6.66mmol) and cesium carbonate (2.82g, 8.7mmol) in ethylene glycol dimethyl ether solution (20mL), add 3 drops at room temperature -Bromopentane (8.64 mL, 8.7 mmol).After the addition was completed, the reaction mixture was refluxed for 2 hours at 80°C.Washed with ethyl acetate and saturated brine. After washing, the organic layers were combined, dried over anhydrous Na2SO4and filtered, and concentrated under reduced pressure under vacuum. The crude product was separated and purified by silica gel column to obtain the intermediate 5-bromo-1-isopentyl. -2(1H)-pyridone, the yield was 69.5%.
	With caesium carbonate In 1,2-dimethoxyethane at 80℃;	A4.1 Method A General procedure: To a stirred solution of 5-bromopyridin-2(1 H)-one (1 1.59 g, 66.6 mmol) in DME (150 mL) was added Cs2C03 (28.2 g, 87 mmol) at RT followed by 2-iodopropane (Fluka) (8.64 mL, 87 mmol). The reaction mixture was heated up and stirred at 80°C for 3 hr. The reaction was diluted with EtOAc and washed with aqueous NaHC03 solution and brine, dried over anhydrous MgS04, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (DCM / MeOH 0 to 20% MeOH) to afford the title product (10.0 g, 46.3 mmol, 69.5% yield). Rt = 0.73 min (UPLC-MS); ESI-MS = 216.0 / 218.0 [M+1]+ (UPLC-MS); 1H NMR (400 MHz, DMSO-cf6) d ppm 1.30 (d, J=6.85 Hz, 6 H) 4.99 (quin, J=6.85 Hz, 1 H) 6.36 (d, J= 9.66 Hz, 1 H) 7.49 (dd, J=9.66, 2.81 Hz, 1 H) 7.97 (d, J=2.81 Hz, 1 H).

Reference： [1]Current Patent Assignee: JIANGSU UNIVERSITY - CN113354631, 2021, A Location in patent: Paragraph 0028
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2019/102256, 2019, A1 Location in patent: Page/Page column 47-48; 51-52

57
[ 1809-10-5 ]
[ 6093-71-6 ]
C₁₇H₂₀O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester With caesium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 3-bromopentane for 12h;	Compound 7h. To a solution of 7f5 (0.07 g, 0.3 mmol) in dryDMF (2 mL) was added cesium carbonate (0.12 g, 0.37 mmol)and the mixture was stirred at room temperature for severalminutes. 3-bromopentane (0.11 mL, 0.89 mmol) was added dropwise to the mixture and stirred for12 h. The reaction was monitored by TLC (MeOH/DCM, 1:9). Upon completion, the product wasextracted with ethyl acetate and washed with H2O, and brine, dried over MgSO4 and concentrated togive the crude product. The product was then isolated by column chromatography on SiO2 usingDCM as eluent to afford compound 7h (0.07 g, 75%).

Reference： [1]Elias, Rebecca; Benhamou, Raphael I.; Jaber, Qais Z.; Dorot, Orly; Zada, Sivan Louzoun; Oved; Pichinuk, Edward; Fridman [European Journal of Medicinal Chemistry, 2019, vol. 179, p. 779 - 790]

58
[ 1809-10-5 ]
C₁₁H₁₀BrNO₂ [ No CAS ]
C₁₆H₂₀BrNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: C₁₁H₁₀BrNO₂ With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Stage #2: 3-bromopentane In N,N-dimethyl-formamide at 60℃;	4.1 Intermediate S75 Compound S64 (5.0 g, 1.0 eq, 0.02 mol) was dissolved in 40 mL of DMF, and NaH (1.20 g, 1.5 eq, 0.03 mol) of a 10 mL DMF suspension was slowly added dropwise at 0 ° C, and stirred at room temperature for 1 hour. Et2CHBr (4.0 mL, 1.5 eq, 0.03 mol) was added to the mixture and stirred at 60 ° C overnight. The water was quenched and extracted with EtOAc.The organic phase was washed with water and aq. Column chromatography (PE: EtOAc = 5:1) gave Compound S75 (3.23 g, yield 50%).

Reference： [1]Current Patent Assignee: Shanghai Institute of Materia Medica (in: CAS); CHINESE ACADEMY OF SCIENCES - CN110016014, 2019, A Location in patent: Paragraph 0114; 0115; 0116

59
[ 1809-10-5 ]
[ 40530-18-5 ]
5-bromo-2-(pentan-3-yloxy)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 5-bromo-2-hydroxybenzonitrile With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3-bromopentane In N,N-dimethyl-formamide at 80℃; for 3h;	6.1 Synthesis of 1-(3-cyano-4-(pentyl-3-oxy)phenyl)-imidazole-4-carboxylic acid (A6) 5-Bromo-2-hydroxy-1-cyanobenzene (1.0 g, 5.0 mmol) was dissolved in DMF (10 mL), After adding K2CO3 (2.1 g, 15.0 mmol) at room temperature for 1.0 h, add 3-bromopentane (2.3 g, 15.0 mmol), and react at 80 °C for 3 h. TLC followed the reaction completely.Cooled to room temperature, diluted with 100mL of water was added, ethyl acetate (100mL × 3). The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure,Purification by silica gel column (V ethyl acetate: V petroleum ether = 1:20) afforded 5-bromo-2-(pentyl-3-oxy)-benzonitrile (a6)1.15 g, yield 85%

Reference： [1]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN110078668, 2019, A Location in patent: Paragraph 0094-0096

60
[ 1809-10-5 ]
[ 5451-40-1 ]
[ 310400-97-6 ]

Yield	Reaction Conditions	Operation in experiment
81.75%	With potassium carbonate In dimethyl sulfoxide at 15℃;	25.1 Step 1 2,6-Dichloro-9- (pent-3-yl) -9H-purine Add 2,6-dichloropurine (1.0g, 5.29mmol), potassium carbonate (2.193g, 15.87mmol), 3-bromopentane (3.286ml, 26.45mmol) to anhydrous DMSO (20ml),The reaction solution was stirred at 15 ° C overnight.After the reaction was monitored by TCL, the reaction solution was poured into ice water, and a white solid precipitated.Filter and dry in vacuo to obtain the target compound 2,6-dichloro-9- (pent-3-yl) -9H-purine.White crystalline solid 1.12g, yield: 81.75%.

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN110903289, 2020, A Location in patent: Paragraph 0223-0227

61
[ 1809-10-5 ]
1-((N,4-dimethylphenyl)sulfonamido)-2-phenylpyridin-1-ium tetrafluoroborate [ No CAS ]
4-(pentan-3-yl)-2-phenylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tris-(trimethylsilyl)silane; sodium acetate In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;

Reference： [1]Hong, Sungwoo; Jung, Sungwoo; Park, Seongjin; Shin, Sanghoon [Journal of the American Chemical Society, 2020, vol. 142, # 26, p. 11370 - 11375]

62
[ 5419-55-6 ]
[ 1809-10-5 ]
[ 7732-18-5 ]
(pentan-3-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: Triisopropyl borate; 3-bromopentane With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 15h; Inert atmosphere; Stage #2: water In tetrahydrofuran	5 Example 5 Add 5mmol of 3-bromopentane to a 150mL two-necked flask, add 80mL of tetrahydrofuran solvent (THF) after removing water and oxygen under a nitrogen atmosphere, and then add 5.5mmol of borate. Stir evenly and place it at -78°C, then add 5.1mmol n-butyllithium dropwise, react at -78 °C for 3h, then return to room temperature for 12h. After the reaction is complete, pour the reaction solution into water. Extract 3 times with dichloromethane, then dry with anhydrous MgSO4, filter, spin-evaporate to remove the solvent, separate and purify with silica gel column, use n-hexane/dichloromethane as eluent, spin-evaporate, dry to remove the solvent to obtain (pentan-3-yl)boronic acid with a yield of 62%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN112321630, 2021, A Location in patent: Paragraph 0069; 0124; 0125

63
[ 1809-10-5 ]
2-bromo-2',4',6'-triisopropyl-6-methyl-[1,1'-biphenyl]-3-ol [ No CAS ]
2-bromo-2’,4’,6’-triisopropyl-6-methyl-3-(3-pentyloxy)-1,1’-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; Schlenk technique; Inert atmosphere;
72%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 15h; Schlenk technique; Inert atmosphere;	26 Synthesis of 2-bromo-2', 4', 6'-triisopropyl-6-methyl-3- (3-pentyroxy) biphenyl Under air, in a 20 mL Schlenk flask, stir bar, 2-bromo-2', 4', 6'-triisopropyl-6-methyl- [1,1'-biphenyl] -3-ol 582 mg (1.5 mmol). , 662 mg (4.5 mmol) of potassium carbonate was added and a flask was attached. The inside of the reaction vessel was replaced with argon, 1.1 mL (9.0 mmol) of 3-bromopentane and 3.0 mL of N, N-dimethylformamide were added, and the mixture was heated and stirred at 100 ° C. for 15 hours. 20 mL of water was added to the reaction solution cooled to room temperature, and the mixture was extracted with 60 mL of diethyl ether. The collected organic phase was washed with 50 mL of saturated brine, added with anhydrous magnesium sulfate and dried, and then the solid was removed by filtration and concentrated. The obtained residue was purified by medium pressure column chromatography (developing solvent = hexane / ethyl acetate) and 2-bromo-2', 4', 6'-triisopropyl-6-methyl-3- (3-pentyloxy). 499 mg of biphenyl was obtained as a white solid (yield 72%).

Reference： [1]Matsushita, Naoki; Kashihara, Myuto; Formica, Michele; Nakao, Yoshiaki [Organometallics, 2021, vol. 40, # 14, p. 2209 - 2214]
[2]Current Patent Assignee: KYOTO UNIVERSITY; TOSOH CORPORATION - JP2021/178811, 2021, A Location in patent: Paragraph 0110-0112

64
[ 1809-10-5 ]
[ 43120-28-1 ]
methyl 1-(pentan-3-yl)-1H-indazole-3-carboxylate [ No CAS ]
methyl 2-(pentan-3-yl)-2H-indazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 48% 2: 46%	Stage #1: methyl 1H-indazole-3-carboxylate With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 3-bromopentane In N,N-dimethyl-formamide at 20℃; for 16h; regioselective reaction;	General Procedure (B) General procedure: To a 50 mL round bottom flask was added the appropriately substituted indazole (1 mmol) andDMF (5 mL). The resulting solution was treated with Cs2CO3 (489 mg, 1.5 mmol) and allowed tostir at room temperature for a further 30 min. To the suspension was added alkylating reagent,R2-X (1.2 mmol), and the mixture was stirred at room temperature for a further 16 h. The reactionmass was diluted with EtOAc (20 mL) and washed with brine (40 mL), sat. aq. Na2S2O3 (10 mL)and brine (40 mL × 2). The organic layer was dried over MgSO4 and concentrated under reducedpressure to afford crude product which was further purified using wet flash columnchromatography to yield the corresponding N-alkylated indazole(s)

Reference： [1]Alam, Ryan M.; Keating, John J. [Beilstein Journal of Organic Chemistry, 2021, vol. 17, p. 1939 - 1951]

65
[ 3558-17-6 ]
[ 1809-10-5 ]
2-methyl-5-nitro-1-(pentyl-3-yl)-1H-indole-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With caesium carbonate In N,N-dimethyl-formamide at 80℃;	56.2 Step 2. 2-Methyl-5-nitro-1-(pentyl-3-yl)-1H-indole-3-carbaldehyde (56c) Compound 56b (2.04g, 10mmol), 3-bromopentane (4.54g, 30mmol), cesium carbonate (8.14g, 30mmol) were dissolved in 10mL of N,N-dimethylformamide,Reaction at 80°C overnight. After the reaction, ethyl acetate and water were added for extraction, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and purified by column chromatography to obtain 904.2 mg of brown solid 56c, with a yield of 33.0%.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Shanghai Institute of Materia Medica (in: CAS); SUN YAT-SEN UNIVERSITY (CHINA) - CN113248481, 2021, A Location in patent: Paragraph 0428; 0430; 0432-0433

66
[ 1809-10-5 ]
[ 22532-62-3 ]
4-(1-ethylpropyl)-2-hydroxybenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-bromopentane With lithium chloride; zinc In tetrahydrofuran at 50℃; for 2h; Stage #2: 4-bromosalicylaldehyde With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran for 10h;	2.3. Synthesis Initially 3-bromopentane ( 1 ) was made to react with Zinc and lithium chloride in minimum amount of THF at 50 °C for 2 h followed by addition of 4-bromo-2-hydroxybenzaldehyde ( 2 ) and Pd(PPh 3 ) 4 and continued to stir for 10 h ( scheme 1 ). The reac- tion was monitored by TLC and on complete consumption of start- ing materials, the resulting reaction mixture was allowed to cool and filtered to get 2-hydroxy-4-(pentan-3-yl)benzaldehyde ( 3 ). Fur- ther, compound 3 was dissolved in minimum amount of DMF along with 1.5 equiv of anhydrous K 2 CO 3 and allowed to react with propargyl bromide, which was added slowly and allowed to stir at room temperature for 16 h to get 2-hydroxy-4-(pentan-3- yl)benzaldehyde ( 4 ). The progress of the reaction was monitored by TLC. Finally, to get the desired product 6 , compound 4 was al- lowed to react with diazidoethane ( 5 ) in presence of copper cat- alyst (10 mol%) using THF:TEA (1:1) as solvent. The crude prod- uct was further purified by column chromatography to get pure compound 6 and thoroughly characterised by NMR and IR. 1,2- diazidoethane ( 5 ) was synthesized according to the reported lit- erature by reaction of 1,3-dibromopropane with sodium azide in DMF [21] .

Reference： [1]Singh, Gurjaspreet; Pawan; Mohit; Diksha; Suman; Priyanka; Sushma; Saini, Anamika; Kaur, Amarjit [Journal of Molecular Structure, 2022, vol. 1250]

67
[ 1809-10-5 ]
[ 479-41-4 ]
(Z)-1'-(pentan-3-yl)-[2,3'-biindolinylidene]-2',3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: indirubin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 22℃; for 0.166667h; Stage #2: 3-bromopentane In N,N-dimethyl-formamide; mineral oil at 90℃; for 16h;

Reference： [1]Dube, Henry; Hoffmann, Nadine; Köttner, Laura; Mayer, Peter; Thumser, Stefan [Journal of the American Chemical Society, 2021, vol. 143, # 43, p. 18251 - 18260]

68
[ 847945-47-5 ]
[ 1809-10-5 ]
penta-3-yl (S)-5-fluoro-3-((R)-5-isopropyl-3-(isoquinolin-1-yl)-4,5 dihydroisoxazole-5-carboxamido)-4-oxopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9%	With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 18h;	21 Example 21: Penta-3-yl (S)-5-fluoro-3-((R)-5-isopropyl-3-(isoquinolin-1-yl)-4,5 dihydroisoxazole-5-carboxamido)-4-oxopentanoate The compound of Formula 2 (0.5 g, 1.2 mmol) was dissolved in dimethylformamide (5 mL), and then 3-bromopentane (0.22 mL, 1.8 mmol, 1.5 equiv) and potassium carbonate (0.2 g, 1.8 mmol, 1.2 equiv) was added thereto. The reaction mixture was stirred at 25°C for about 18 hours, diluted in ethyl acetate (EtOAc, 30 mL), and 10% aqueous sodium hydrogen carbonate solution (30 mL) was added and reacted with stirring. After adding water (30 mL) and stirring, the organic layer was separated and distilled under reduced pressure. The obtained mixture was subjected to column separation by the use of a 1:2 mixture of ethyl acetate and hexane (EtOAc: hexane=1:2) to obtain 0.05 g (yield: 9%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 9.14 (d, 1H), 8.56 (d, 1H), 7.88 (d, 1H), 7.75-7.66 (m, 4H), 5.20 (m, 2H), 4.95 (m, 1H), 4.76 (m, 1H), 4.03 (d, 1H), 3.82 (d, 1H), 3.01 (dd, 2H), 2.40 (m, 1H), 1.54 (m, 4H), 1.10 (dd, 6H), 0.86 (t, 6H)
9%	With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 18h;	21 Example 21: Penta-3-yl (S)-5-fluoro-3-((R)-5-isopropyl-3-(isoquinolin-1-yl)-4,5 dihydroisoxazole-5-carboxamido)-4-oxopentanoate The compound of Formula 2 (0.5 g, 1.2 mmol) was dissolved in dimethylformamide (5 mL), and then 3-bromopentane (0.22 mL, 1.8 mmol, 1.5 equiv) and potassium carbonate (0.2 g, 1.8 mmol, 1.2 equiv) was added thereto. The reaction mixture was stirred at 25°C for about 18 hours, diluted in ethyl acetate (EtOAc, 30 mL), and 10% aqueous sodium hydrogen carbonate solution (30 mL) was added and reacted with stirring. After adding water (30 mL) and stirring, the organic layer was separated and distilled under reduced pressure. The obtained mixture was subjected to column separation by the use of a 1:2 mixture of ethyl acetate and hexane (EtOAc: hexane=1:2) to obtain 0.05 g (yield: 9%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 9.14 (d, 1H), 8.56 (d, 1H), 7.88 (d, 1H), 7.75-7.66 (m, 4H), 5.20 (m, 2H), 4.95 (m, 1H), 4.76 (m, 1H), 4.03 (d, 1H), 3.82 (d, 1H), 3.01 (dd, 2H), 2.40 (m, 1H), 1.54 (m, 4H), 1.10 (dd, 6H), 0.86 (t, 6H)
9%	With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 18h;	21 Example 21: Penta-3-yl (S)-5-fluoro-3-((R)-5-isopropyl-3-(isoquinolin-1-yl)-4,5 dihydroisoxazole-5-carboxamido)-4-oxopentanoate The compound of Formula 2 (0.5 g, 1.2 mmol) was dissolved in dimethylformamide (5 mL), and then 3-bromopentane (0.22 mL, 1.8 mmol, 1.5 equiv) and potassium carbonate (0.2 g, 1.8 mmol, 1.2 equiv) was added thereto. The reaction mixture was stirred at 25°C for about 18 hours, diluted in ethyl acetate (EtOAc, 30 mL), and 10% aqueous sodium hydrogen carbonate solution (30 mL) was added and reacted with stirring. After adding water (30 mL) and stirring, the organic layer was separated and distilled under reduced pressure. The obtained mixture was subjected to column separation by the use of a 1:2 mixture of ethyl acetate and hexane (EtOAc: hexane=1:2) to obtain 0.05 g (yield: 9%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 9.14 (d, 1H), 8.56 (d, 1H), 7.88 (d, 1H), 7.75-7.66 (m, 4H), 5.20 (m, 2H), 4.95 (m, 1H), 4.76 (m, 1H), 4.03 (d, 1H), 3.82 (d, 1H), 3.01 (dd, 2H), 2.40 (m, 1H), 1.54 (m, 4H), 1.10 (dd, 6H), 0.86 (t, 6H)

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - EP3954683, 2022, A1 Location in patent: Paragraph 0112-0114
[2]Current Patent Assignee: LG CHEM CO.,LTD. - EP3954683, 2022, A1 Location in patent: Paragraph 0112-0114
[3]Current Patent Assignee: LG CHEM CO.,LTD. - EP3954683, 2022, A1 Location in patent: Paragraph 0112-0114

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	1809-10-5	MDL No. :	MFCD00000158
Formula :	C₅H₁₁Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VTOQFOCYBTVOJZ-UHFFFAOYSA-N
M.W :	151.04	Pubchem ID :	15738
Synonyms :

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.02
TPSA :	0.0 Å²

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.2 cm/s

[ CAS No. 1809-10-5 ]

Quality Control of [ 1809-10-5 ]

Related Doc. of [ 1809-10-5 ]

Product Details of [ 1809-10-5 ]

Calculated chemistry of [ 1809-10-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1809-10-5 ]

Application In Synthesis of [ 1809-10-5 ]

[ 1809-10-5 ] Synthesis Path-Upstream 1~2

[ 1809-10-5 ] Synthesis Path-Downstream 1~68

Related Functional Groups of
[ 1809-10-5 ]

Aliphatic Chain Hydrocarbons

Bromides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

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Inquiry

Log Po/w (iLOGP) :	2.28
Log Po/w (XLOGP3) :	2.84
Log Po/w (WLOGP) :	2.57
Log Po/w (MLOGP) :	2.78
Log Po/w (SILICOS-IT) :	1.84
Consensus Log Po/w :	2.46

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.43
Solubility :	0.556 mg/ml ; 0.00368 mol/l
Class :	Soluble
Log S (Ali) :	-2.5
Solubility :	0.48 mg/ml ; 0.00317 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.35
Solubility :	0.681 mg/ml ; 0.00451 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.26

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P233-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501	UN#:	1993
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅱ
GHS Pictogram:

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Response
Code	Phrase
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P320
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P321
P322
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
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P411
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P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 1809-10-5 ]

Quality Control of [ 1809-10-5 ]

Related Doc. of [ 1809-10-5 ]

Product Details of [ 1809-10-5 ]

Calculated chemistry of [ 1809-10-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1809-10-5 ]

Application In Synthesis of [ 1809-10-5 ]

[ 1809-10-5 ] Synthesis Path-Upstream 1~2

[ 1809-10-5 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 1809-10-5 ]

Aliphatic Chain Hydrocarbons

Bromides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1809-10-5 ]