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[ CAS No. 84249-14-9 ]

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Chemical Structure| 84249-14-9
Chemical Structure| 84249-14-9
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CAS No. :84249-14-9MDL No. :MFCD01646115
Formula : C5H5BrN2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :173.01Pubchem ID :693282
Synonyms :

Computed Properties of [ 84249-14-9 ]

TPSA : 38.9 H-Bond Acceptor Count : 2
XLogP3 : 1.2 H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 84249-14-9 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P305+P351+P338UN#:N/A
Hazard Statements:H302-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 84249-14-9 ]

  • Upstream synthesis route of [ 84249-14-9 ]
  • Downstream synthetic route of [ 84249-14-9 ]

[ 84249-14-9 ] Synthesis Path-Upstream   1~14

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  • [ 84249-14-9 ]
  • [ 1095708-32-9 ]
Reference: [1] Patent: US2014/194443, 2014, A1,
[2] Patent: WO2014/108337, 2014, A1,
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5613 - 5637
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  • [ 84249-14-9 ]
  • [ 24424-99-5 ]
  • [ 1095708-32-9 ]
Reference: [1] Patent: WO2016/124508, 2016, A1,
  • 3
  • [ 84249-14-9 ]
  • [ 1187449-01-9 ]
YieldReaction ConditionsOperation in experiment
61% With N-chloro-succinimide In N,N-dimethyl-formamide at -20 - 20℃; for 24 h; [00252j 27A. 4-Bromo-5-chloropyridin-2-amine: To a stirred solution of 4-bromopyridin-2-amine (30.0 g, 173 mmol) in DMF (350 mL) at -20 °C was added 1-chloropyrrolidine-2,5-dione (24.3 g, 182 mmol). The reaction mixture was stirred at rtfor 24 h. The reaction mixture was poured into cold 1 M aq. NaOH (300 mL) andextracted with Et20 (2 x 400 mL). The combined extracts were washed with water (3 x200 mL), brine (200 mL), dried over Na2SO4, filtered, and concentrated. The crudematerial was recrystallized from CH2C12 to provide 27A as red solid (22.0 g, 106 mmol,61percent yield). LC-MS Anal. Calc’d for C5H4BrC1N2: 205.93, found [M+H] 206.9.
61% With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃; for 24 h; 81A.
4-Bromo-5-chloropyridin-2-amine
To a stirred solution of 4-bromopyridin-2-amine (30 g, 173 mmol) in DMF (350 mL) at -20° C. was added 1-chloropyrrolidine-2,5-dione (24 g, 182 mmol).
The reaction mixture was allowed to stir at rt for 24 h.
The reaction mixture was poured into a cold solution of 1M NaOH (300 mL) and the mixture was extracted with Et2O (2*400 mL).
The combined extracts were washed with water (3*200 mL), brine (200 mL), dried over Na2SO4, filtered and concentrated.
The crude material was recrystallized from DCM which afforded 4-bromo-5-chloropyridin-2-amine as red solid (22 g, 106 mmol, 61percent yield). LC-MS Anal.
Calc'd for C5H4BrClN2 205.93. found [M+H] 206.9. 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 6.81 (s, 1H), 4.49 (br. s., 2H).
61% With N-chloro-succinimide In N,N-dimethyl-formamide at -20 - 20℃; Inert atmosphere Description 14 (D14); 4-bromo-5-chloro-2-pyridinamine; To a stirred solution of 2-amino-4-bromopyridine (15.0 g, 86.7 mmol) in N, N- dimethylformamide (430 ml_) at -200C was added N-chlorosuccinimide (12.99 g, 95.34 mmol). Reaction mixture allowed to stir at room temperature for 24 h. Reaction mixture poured into cold 1 M sodium hydroxide (750 ml_) and extracted with diethyl ether (4 x 500 ml_). The combined extracts were washed with water (3 x 200 ml_), brine (200 ml_), dried over sodium sulfate, filtered and solvent removed in vacuo yielding a solid (17.2 g) which was recrystallised from hexane to yield a solid (12.8 g). Material purified by column <n="70"/>chromatography eluting with 0-25percent ethyl acetate in dichloromethane. The relevant fractions were combined and solvent removed in vacuo to furnish the title compound (1 1.0 g, 61 percent). 1H NMR: (300 MHz, CDCI3) δ 8.05 (s, 1 H), 6.79 (s, 1 H), 4.49 (s, 2H).
43.7% With N-chloro-succinimide In N,N-dimethyl-formamide at -78 - 20℃; Inert atmosphere N-Chloro-succinimide (3.70 g, 27.7 mmol) dissolved in DMF (20 mL) was added dropwise to 4-bromopyridin-2-amine (4.40 g, 25.4 mmol) in DMF (50 mL) at −78° C. over a period of 30 minutes under nitrogen. The resulting suspension was then allowed to warm to r.t. After stirring under these conditions for 24 h, the reaction mixture was diluted with Et2O (50 mL) and washed sequentially with 1 M aqueous NaOH (2×50 mL), water (50 mL), and saturated aqueous sodium chloride (25 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting crude product was purified by flash silica chromatography, elution gradient 0 to 25percent EtOAc in DCM. Pure fractions were evaporated to dryness to afford 4-bromo-5-chloropyridin-2-amine (2.30 g, 43.7percent) as a cream solid. 1H NMR (400 MHz, DMSO-d6, 30° C.) 6.35 (2H, s), 6.82 (1H, s), 8.01 (1H, s). m/z: ES+[M+H]+ 209 (35C1 81Br and 37C1 79Br isotopes).

Reference: [1] Patent: WO2014/78609, 2014, A1, . Location in patent: Paragraph 00252
[2] Patent: US9133163, 2015, B2, . Location in patent: Page/Page column 89; 90
[3] Patent: WO2009/112473, 2009, A1, . Location in patent: Page/Page column 68-69
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 8, p. 2552 - 2555
[5] Patent: US2016/376287, 2016, A1, . Location in patent: Paragraph 0624
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9663 - 9679
[7] Patent: WO2014/139328, 2014, A1, . Location in patent: Page/Page column 381
[8] Patent: US2014/275011, 2014, A1, . Location in patent: Paragraph 1521
[9] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 19 - 32
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  • [ 1186115-39-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8712 - 8735
[2] Patent: WO2009/147440, 2009, A1, . Location in patent: Page/Page column 55-56
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  • [ 84249-14-9 ]
  • [ 1053655-66-5 ]
Reference: [1] Patent: US2011/98471, 2011, A1,
  • 6
  • [ 84249-14-9 ]
  • [ 75-36-5 ]
  • [ 1026796-81-5 ]
YieldReaction ConditionsOperation in experiment
95% With pyridine In dichloromethane at 20℃; Inert atmosphere 4-Bromopyridin-2-amine (10 g, 57.8 mmol) was taken up in DCM (75 mL) and pyridine (75 mL) under nitrogen. Acetic anhydride (8.18 mL, 87 mmol) was added and the reaction stirred at room temperature. The reaction was left to stand overnight and then concentrated in vacuo. The residue was dried in the vac oven to give A/-(4-bromopyridin-2-yl)acetamide (12.4 g, 54.8 mmol, 95 percent yield) as a cream solid. 1H NMR (400MHz, CDCI3) δ-ppm 8.48 (1 H, s), 8.14 (1 H, br. s), 8.09 (1 H, d), 7.23 (1 H, dd), 2.23 (3H, s). LCMS (2 min, Formic): Rt = 0.65 min, MhT 215/217.
95% With pyridine In dichloromethane at 0 - 20℃; for 2 h; To a mixture of 4-bromopyridin-2-amine (3.11 g, 17.98 mmol) in CH2Cl2 (60 mL) at 0 °C was added acetyl chloride (1.406 mL, 19.77 mmol) and pyridine (1.745 mL, 21.57 mmol). The mixture was warmed to rt and stirred for 2 h. The reaction was quenched with water and diluted with EtOAc. The layers were separated. The organic layer was washed with water, brine, dried (Na2S04) and concentrated under reduced pressure to obtain N-(4-bromopyridin-2-yl)acetamide (3.82 g, 17.05 mmol, 95percent yield) as a white solid. The material was carried on without further purification. LCMS (ESI) m/e 215.0 [(M+H)+, calcd C7H8Br1N2O1, 215.0]; LC/MS retention time (method A): = 2.61 min.
95% With pyridine In dichloromethane at 0 - 20℃; for 2 h; To a mixture of 4-bromopyridin-2-amine (3.11 g, 17.98 mmol) in CH2CI2 (60 mL) at 0 °C was added acetyl chloride (1.406 mL, 19.77 mmol) and pyridine (1.745 mL, 21.57 mmol). The mixture was warmed to rt and stirred for 2 h. The reaction was quenched with water and diluted with EtOAc. The layers were separated. The organic layer was washed with water, brine, dried Na2S04) and concentrated under reduced pressure to obtain N-(4-bromopyridin-2-yl)acetamide (3.82 g, 17.05 mmol, 95percent yield) as a white solid. The material was carried on without further purification. LCMS (ESI) m/e 215.0 [(M+H)+, calcd 215.0]; LC/MS retention time (method A): /R = 2.61 min.
81%
Stage #1: With pyridine In dichloromethane at 20℃; for 0.333333 h;
Stage #2: at 20℃;
Pyridine (0.374 mL, 4.62 mmol) was added to a solution of 4-bromopyridin-2-amine (400 mg, 2.312 mmol) in DCM (10 mL) and stirred at rt for 20 min. Acetyl chloride (0.190 mL, 2.66 mmol) was added and the solution was stirred at rt overnight. Water was added and the product was extracted with DCM. The organic layer was washed with brine, filtered through a hydrophobic frit, and concentrated in vacuo. The residue was dissolved in MeOH and passed through a 10 g aminopropyl column, eluting with MeOH. The solvent was evaporated give the title compound as a white solid (404 mg, 1.879 mmol, 81 percent yield). LCMS (2 min, High pH): Rt = 0.65 min, MH+ = 215/217.
72.4% With pyridine In dichloromethane at 0 - 20℃; for 5.33333 h; To a solution of 4-bromopyridin-2-amine (4 g, 23.12 mmol) in DCM (40 mL), cooled to 0 °C was added pyridine (2.80 mL, 34.7 mmol) dropwise over a period of 10 min. The reaction mixture was stirred for 10 min at 0 °C, then acetyl chloride (2.137 mL, 30.1 mmol) was added slowly. The reaction mixture was stirred at 0 °C for 1 h and brought to room temperature. After stirring at room temperature for 4 h the reaction mixture was diluted with water (20 mL) and extracted with DCM (2 x 20 mL). The combined organic layers were concentrated under reduced pressure to afford N-(4-bromopyridin-2-yl)acetamide (3.6 g, 16.74 mmol, 72.4 percent yield) as a light brown solid. LCMS (ESI) m/e 215.0, 217.0 Br pattern [(M+H)+, calcd for C7H8BrN20, 215.0]; LC/MS retention time (method E): tR = 1.55 min.
66%
Stage #1: With pyridine In dichloromethane at 0℃; for 0.166667 h;
Stage #2: at 0 - 20℃;
To a solution of 4-bromopyridin-2-amine (5.0 g, 29.07 mmol) in dichloromethane (50 mL) cooled to 0 °C was added pyridine (3.5 mL, 43.4 mmol) and the solution was stirred for 10 min. Acetyl chloride (2.1 mL, 29.5 mmol) was added. The reaction mixture was allowed to stir at 0 °C for 30 min. Then the reaction mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with brine (50 mL). The aqueous layer was extracted with dichloromethane (3 x 200 mL). The organic layer was dried over Na2S04, filtered and concentrated under reduced to afford the title compound (4.1 g, 19.2 mmol, 66percent> yield) as a light yellow solid. LCMS (ESI) m/e 215.0 [(M+H)+, calcd for C7H8BrN20, 215.0]; LC/MS retention time (method F): tR = 1.53 min.
33% With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere Under the protection of N2 gas at 0° C., add acetyl chloride (454 mg, 5.8 mmol) into the solution of 4-bromo-2-aminopyridine (1.0 g, 5.8 mmol) and triethylamine (1.75 g, 17 mmol) in dichloromethane (50 ml). Allow the solution to react 1 hour at room temperature. Then pour it into ice water (50 ml) to quench before extract with dichloromethane (20 ml). Combine the organic layers and dry it with anhydrous Na2SO4 before filter and evaporate. Separate and purify the crude product with column chromatography (petroleum ether:ethyl acetate=5:1) to obtain the title compound (white solid, 400 mg, 33percent). 1H NMR(400 MHz,CHLOROFORM-d)8.38-8.53(m,1H),8.08(d,J=5.02 Hz,1H),7.93(br.s.,1H),7.21(d,J=4.52 Hz,1H),2.22(s, 3H).

Reference: [1] Patent: WO2014/140077, 2014, A1, . Location in patent: Page/Page column 60
[2] Patent: WO2015/153720, 2015, A1, . Location in patent: Page/Page column 20; 21
[3] Patent: WO2017/59085, 2017, A1, . Location in patent: Page/Page column 20; 21
[4] Patent: WO2014/78257, 2014, A1, . Location in patent: Page/Page column 118
[5] Patent: WO2015/116492, 2015, A1, . Location in patent: Page/Page column 80
[6] Patent: WO2016/22312, 2016, A1, . Location in patent: Page/Page column 106
[7] Patent: US2017/66732, 2017, A1, . Location in patent: Paragraph 0391-0392
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  • [ 108-24-7 ]
  • [ 1026796-81-5 ]
YieldReaction ConditionsOperation in experiment
98.14% at 20℃; Industrial scale To a 1 L four-necked flask equipped with a magnetic stirrer and thermometer, 45.84 g (0.265 mol)2-amino-4-bromopyridine, was added 500mL dichloromethane at room temperature with stirring to dissolve slowly added dropwise 40.52 g (0.397mol) acetic anhydride, the completion of the reaction for 2 to 5 hours,The reaction was completed by TLC until the reaction was completed. The residue was distilled under reduced pressure. The residue was dissolved in ethyl acetate and washed twice with 200 mL of saturated sodium bicarbonate. The residue was evaporated to dryness to give 55.91 g of 2-acetylamino-4-bromopyridine. The yield was 98.14percent.
89% at 140℃; for 3 h; 00115 To a solution of 4-bromopyridin-2-amine (12.0 g, 69.4 mmol) in acetic anhydride (240 mL) was added DMAP (0.0847 g, 0.694 mmol). The reaction mixture was allowed to stir at 140 °C for 3 h and then allowed to cool to rt. Ice water was added and the pH of the mixture was adjusted to 8.5 by the addition of concentrated NH4OH. The solid which precipitated was filtered, washed with cold water and hexanes, and dried to give N-(4-bromopyridin-2-yl)acetamide (13.3 g, 89percent) as a white solid.
89% at 140℃; for 3 h; [00179] To a solution of 4-bromopyridin-2-amine (12.0 g, 69.4 mmol) in acetic anhydride (240 mL) was added DMAP (0.0847 g, 0.694 mmol). The reaction mixture was allowed to stir at 140°C for 3 h and then allowed to cool tort. Ice water was added and the pH of the mixture was adjusted to 8.5 by the addition of concentrated NFI4OH. The solid which precipitated was filtered, washed with cold water and hexanes, and dried to give N-(4-bromopyridin-2-yl)acetamide (13.3 g, 89percent) as a white solid.
89% at 140℃; for 3 h; Step 1:
N-(4-bromopyridin-2-yl)acetamide
To a solution of 4-bromopyridin-2-amine (12.0 g, 69.4 mmol) in acetic anhydride (240 mL) was added DMAP (0.0847 g, 0.694 mmol).
The reaction mixture was allowed to stir at 140° C. for 3 h and then allowed to cool to rt.
Ice water was added and the pH of the mixture was adjusted to 8.5 by the addition of concentrated NH4OH.
The solid which precipitated was filtered, washed with cold water and hexanes, and dried to give N-(4-bromopyridin-2-yl)acetamide (13.3 g, 89percent) as a white solid.
89% at 140℃; for 3 h; Step 1:
N-(4-bromopyridin-2-yl)acetamide
To a solution of 4-bromopyridin-2-amine (12.0 g, 69.4 mmol) in acetic anhydride (240 mL) was added DMAP (0.0847 g, 0.694 mmol).
The reaction mixture was allowed to stir at 140° C. for 3 h and then allowed to cool to rt.
Ice water was added and the pH of the mixture was adjusted to 8.5 by the addition of concentrated NH4OH.
The solid which precipitated was filtered, washed with cold water and hexanes, and dried to give N-(4-bromopyridin-2-yl)acetamide (13.3 g, 89percent) as a white solid.
88% at 140℃; for 1 h; Sealed tube To a mixture of 4-bromopyridin-2-amine (3.8 g, 22 mmol) in Ac2O (20 mL) was added DMAP (0.054 g, 0.44 mmol). The mixture was heated in a sealed pressure reaction vessel at 140° C. for 1 h, and then cooled to room temperature. The reaction mixture was poured into ice-water, and the resulting mixture was adjusted to pH=8.4 with NH4OH. The resulting precipitate was collected by filtration, washed with water and dried to afford Example 1A (4.2 g, 88percent). HPLC: RT=0.587 min (H2O/MeOH with 0.1percent TFA, Chromolith SpeedROD, 4.6×50 mm, gradient=4 min, wavelength=220 nm); MS (ES): m/z=217 [M+H]+; 1H NMR (400 MHz, Chloroform-d) δ ppm 10.71 (br. s., 1H), 8.32 (d, J=0.1.8 Hz, 1H), 8.22 (d, J=5.5 Hz, 1H), 7.35 (dd, J=5.3, 1.8 Hz, 1H), 2.11 (s, 3H).
77%
Stage #1: at 140℃; for 3 h;
Stage #2: at 20℃; Cooling with ice
Step 1:
N-(4-bromopyridin-2-yl)acetamide Intermediate 19
To a solution of 4-bromopyridin-2-amine (0.9 g, 5.2 mmol) in acetic anhydride (18 mL, 191 mmol) was added N,N-dimethylaminopyridine (0.006 g, 0.052 mmol).
The reaction mixture was stirred at 140° C. for 3 h.
The reaction mixture was cooled to rt and ice water (50 mL) was added followed by conc. NH4OH (~60 mL) to adjust the pH to 8.5.
A white solid precipitated and was isolated by filtration.
This solid was washed with cold water and then hexanes.
The solid was dried under high vacuum to afford N-(4-bromopyridin-2-yl)acetamide (858 mg, 77percent) LC-MS (FA) ES+ 216.
13.3 g at 140℃; for 3 h; Step 1:
N-(4-bromopyridin-2-yl)acetamide
To a solution of 4-bromopyridin-2-amine (12.0 g, 69.4 mmol) in acetic anhydride (240 mL) was added DMAP (0.0847 g, 0.694 mmol).
The reaction mixture was allowed to stir at 140° C. for 3 h and then allowed to cool to rt.
Ice water was added and the pH of the mixture was adjusted to 8.5 by the addition of concentrated NH4OH.
The solid which precipitated was filtered, washed with cold water and hexanes, and dried to give N-(4-bromopyridin-2-yl)acetamide (13.3 g) as a white solid.

Reference: [1] Patent: CN103601745, 2017, B, . Location in patent: Paragraph 0023; 0024
[2] Patent: WO2015/108881, 2015, A1, . Location in patent: Paragraph 00115
[3] Patent: WO2015/108861, 2015, A1, . Location in patent: Paragraph 00179
[4] Patent: US2015/225422, 2015, A1, . Location in patent: Paragraph 0235-0236
[5] Patent: US2016/333007, 2016, A1, . Location in patent: Paragraph 0226
[6] Patent: US2016/176871, 2016, A1, . Location in patent: Paragraph 0344-0345
[7] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 11, p. 1117 - 1122
[8] Patent: US2012/15943, 2012, A1, . Location in patent: Page/Page column 55
[9] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5613 - 5637
[10] Patent: US2013/165464, 2013, A1, . Location in patent: Paragraph 0834
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  • [ 127-19-5 ]
  • [ 1026796-81-5 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 14, p. 10567 - 10574
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  • [ 84249-14-9 ]
  • [ 1019021-93-2 ]
Reference: [1] Patent: WO2013/30802, 2013, A1,
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  • [ 84249-14-9 ]
  • [ 1134327-98-2 ]
YieldReaction ConditionsOperation in experiment
22% With sulfuric acid In ethanol at 0 - 80℃; for 5 h; To a solution of sulfuric acid (4.54 g, 46.24 mmol, 2.46 mL, 1.6 eq) and ethanol (75 mL) at 0 °C was added Example 102A (16.90 g, 89.59 mmol, 3.1 eq) and 2-amino-4- bromopyridine (5.00 g, 28.90 mmol, 1 eq). The reaction was stirred at 80 °C for 5 hr. The reaction was cooled to 25 °C and was diluted with water. The aqueous solution was adjusted to pH=7, and extracted with ethyl acetate (300 mL*3). The combined organic phase was washed with brine (200 mL*2), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography. Example 102B (1.70 g, 6.32 mmol, yield =22percent) was obtained as a white solid. (0193) [0114] MR: (CDCb, 400MHz): ppm 9.19 (d, J=7.2 Hz, 1H), 8.27 (s, 1H), 7.93 (s, 1H), 7.16 (dd, J=1.6, 7.6 Hz, 1H), 4.43 (q, J=7.6 Hz, 2H), 1.43 (t, J=7.2 Hz, 3H).
Reference: [1] Patent: WO2017/214413, 2017, A1, . Location in patent: Paragraph 0113-0114
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  • [ 84249-14-9 ]
  • [ 33142-21-1 ]
  • [ 1134327-98-2 ]
Reference: [1] Patent: WO2011/79076, 2011, A1, . Location in patent: Page/Page column 66; 67
[2] Patent: WO2012/87519, 2012, A1, . Location in patent: Page/Page column 112
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  • [ 84249-14-9 ]
  • [ 1426531-64-7 ]
  • [ 1134327-98-2 ]
Reference: [1] Patent: WO2013/30802, 2013, A1, . Location in patent: Page/Page column 121; 122
[2] Patent: WO2014/132220, 2014, A1, . Location in patent: Page/Page column 40
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  • [ 84249-14-9 ]
  • [ 1066-54-2 ]
  • [ 1094679-27-2 ]
YieldReaction ConditionsOperation in experiment
33% With bis(benzonitrile)palladium(II) dichloride; caesium carbonate; triethylamine; [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane In N,N-dimethyl-formamide at 50℃; for 2 h; Compound 2 (400 mg, 2.31 mmol), trimethylsilylacetylene (0.38 ml, 2.77 mmol), cesium carbonate (39.1 mg, 0.12 mmol), 4,5- bis (diphenylphosphino) -9,9-dimethylxanthene (69.4 mg , 0.12 mmol) and was dissolved bis (benzonitrile) palladium (II) dichloride (46.0 mg, a 0.12 mmol) in DMF (5 ml). Further added triethylamine (2 ml) to this was stirred for 2 hours at 50 in an oil bath. After completion of the reaction, THF and (3 ml) and tetrabutylammonium fluoride (2.77 ml) was added and the solvent was concentrated under reduced pressure, and allowed to react for 30 minutes at room temperature. The solvent was evaporated, adsorbed resulting residue was applied to a silica gel column,Methanol - was eluted with a mixed solvent of chloroform (1:50) to give Compound 5a (90.1 mg, 33percent).
Reference: [1] Patent: JP2015/221769, 2015, A, . Location in patent: Paragraph 0031; 0033
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Reference: [1] Letters in Drug Design and Discovery, 2011, vol. 8, # 5, p. 401 - 405
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