1583272-35-8|Methyl 6-bromo-3-methyl-1H-indole-4-carboxylate| Ambeed

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1
[ 1922199-96-9 ]
[ 1583272-35-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With bis-triphenylphosphine-palladium(II) chloride; tetrabutyl-ammonium chloride; sodium acetate; triphenylphosphine In N,N-dimethyl-formamide at 100℃;	43 synthesis of 6-Bromo-3-methyl -1H- indol-4-carboxylate The 2.0g (6.87mmol) 3- (allylamine) -2,5-bromobenzoate was dissolved in DMF and phase transfer catalyst tetrabutylammonium chloride (332mg, 1.03mmol, 15mmol %) and triphenyl phosphite ligand (85mg, 0.27mmol, 4mmol%) ,and sodium acetate was added bis (tricyclohexylphosphine) palladium dichloride (200mg, 0.27mmol, 4mmol%) ,and the 100 The reaction conditions under overnight; the reaction solution after treatment and purification, to give the product 0.89g (58% yield); Other conditions as in Example 36, to change the phase transfer catalyst is tetrabutylammonium chloride, the resulting product in 67% yield.
53%	With tetrabutylammomium bromide; potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere;	Methyl 6-bromo-3-methyl-1H-indole-4-carboxylate(6) To a stirred solution of 5 (4.3g, 12.3 mmol) in DMF (50 mL) was added Pd(OAc)2 (276mg, 1.2 mmol, 0.1 equiv), KOAc (1.8g,18.5 mmol, 1.5 equiv) and TBAB (596mg, 1.9 mmol, 0.15 equiv) under a stream of argon. After the mixture was heated at 100°C with stirring for 1 h, the solvent was removed in vacuo, and the residue was then extracted with DCM (3×50 mL), washed with H2O (2×30 mL) and brine (30 mL), and dried (MgSO4). The crude product was purified by flash column chromatography (eluting with hexanes/EtOAc, 20:1) to get indole 6 (1.72g, 53% yield) as a solid, m.p. 72-75°C. 1H NMR (CDCl3,300 MHz): δ2.36 (s3H), 3.95 (s, 3H), 7.02 (s, 1H), 7.54 (d, J=1.1 Hz, 1H), 7.71 (d, J=1.1Hz, 1H), 8.33 (s, 1H); 13C NMR (CDCl3, 75 MHz): δ13.2, 52.2, 112.6, 113.8, 117.8, 124.4, 125.8,138.5, 167.8; HRMS (ESI): m/z calcd. for C11H10BrNO2Na [M+Na]+ 289.9793, found 289.9785.

Reference： [1]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN105541801, 2016, A Location in patent: Paragraph 0078
[2]Lu, Chen; Zhang, Qiang; Chen, Xin [Synthetic Communications, 2016, vol. 46, # 14, p. 1215 - 1222]

2
[ 1583272-35-8 ]
[ 1346574-54-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium hydroxide / dimethyl sulfoxide / 6 h / 20 °C / Inert atmosphere 2: sodium hydroxide; methanol / tetrahydrofuran; water / 24 h / 20 °C / Inert atmosphere 3: 1-hydroxy-7-aza-benzotriazole; 1,2-dichloro-ethane; 4-methyl-morpholine / dimethyl sulfoxide / 36 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: triethylamine; methylene chloride; sodium hydroxide / N,N-dimethyl-formamide / 20 °C 2: sodium hydroxide / methanol; water 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole / 80 °C

Reference： [1]Lu, Chen; Zhang, Qiang; Chen, Xin [Synthetic Communications, 2016, vol. 46, # 14, p. 1215 - 1222]
[2]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN105541801, 2016, A

3
6-bromo-3-methyl-1H-indole-4-carboxylic acid methyl ester [ No CAS ]
[ 1346574-57-9 ]

Reference： [1]Synthetic Communications,2016,vol. 46,p. 1215 - 1222
[2]Patent: CN105541801,2016,A

4
[ CAS Unavailable ]
[ 1583272-35-8 ]
[ 1922199-97-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium hydroxide In dimethyl sulfoxide at 20℃; for 6h; Inert atmosphere;	(S)-Methyl 6-bromo-1-(sec-butyl)-3-methyl-1H-indole-4-carboxylate (7) TsCl (2.2g, 11.5 mmol) was added to a solution of (R)-isobutanol (775mg, 10.5 mmol), Et3N (1.6g, 15.8 mmol) and DCM (30 mL) at 0°C, and the mixture was stirred at the same temperature for 4h. The organic layer was separated, and the aqueous layer was extracted with DCM (2×50mL). The combined organic layers were washed with H2O (2×20 mL) and brine (30 mL), and dried (MgSO4). The solvent was removed, and the residue was purified by flash column chromatography (eluting with hexane/EtOAc, 50:1) to obtain (R)-sec-butyl 4-methylbenzenesulfonate (1.46g). The tosylate obtained above (1.46g, 6.4mmol) was dissolved in DMSO (11 mL), and indole 6 (1.14g, 4.3 mmol) and KOH (2.17g, 38.7 mmol) was added, and the mixture was stirred at rt for 6h. After completion of the reaction, 3N HCl (20 mL) was added to the reaction mixture to adjust the pH to 3-4. The resulting mixture was extracted with EtOAc (2×50 mL), and the combined organic layers were washed with H2O (2×20mL) and brine (30 mL), and dried (MgSO4). The crude product was purified by flash column chromatography (eluting with hexane/EtOAc, 20:1) to obtain 7 (1.28g, 92% yield) as white powder; m.p. 36-37°C; 96.5% ee, [α]25D +1.8° (c=0.1, CH2Cl2). 1H NMR (CDCl3, 400 MHz): δ 0.82 (t, J=7.4 Hz, 3H),1.47 (d, J=6.4 Hz, 3H), 1.86 (m, 2H),2.36 (s, 3H), 3.95 (s, 3H), 4.26-4.32 (m, 1H), 7.04 (s, 1H), 7.61 (d, J=1.2 Hz, 1H), 7.67 (d, J=2.0 Hz, 1H); 13C NMR (CDCl3, 100 MHz): δ 10.9, 13.2, 21.0, 30.0, 52.1, 53.1, 111.4, 113.4,115.8, 124.4, 124.5, 125.3, 138.6, 167.8; HRMS (ESI): m/z calcd. for C15H18BrNO2 [M-H]+ 324.0594, found 324.0601.

Reference： [1]Lu, Chen; Zhang, Qiang; Chen, Xin [Synthetic Communications, 2016, vol. 46, # 14, p. 1215 - 1222]

5
[ 50896-54-3 ]
[ 1583272-35-8 ]
[ 1975114-32-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium hydroxide In dimethyl sulfoxide at 20℃; for 6h; Inert atmosphere;	(S)-Methyl 6-bromo-1-(sec-butyl)-3-methyl-1H-indole-4-carboxylate (7) General procedure: TsCl (2.2g, 11.5 mmol) was added to a solution of (R)-isobutanol (775mg, 10.5 mmol), Et3N (1.6g, 15.8 mmol) and DCM (30 mL) at 0°C, and the mixture was stirred at the same temperature for 4h. The organic layer was separated, and the aqueous layer was extracted with DCM (2×50mL). The combined organic layers were washed with H2O (2×20 mL) and brine (30 mL), and dried (MgSO4). The solvent was removed, and the residue was purified by flash column chromatography (eluting with hexane/EtOAc, 50:1) to obtain (R)-sec-butyl 4-methylbenzenesulfonate (1.46g). The tosylate obtained above (1.46g, 6.4mmol) was dissolved in DMSO (11 mL), and indole 6 (1.14g, 4.3 mmol) and KOH (2.17g, 38.7 mmol) was added, and the mixture was stirred at rt for 6h. After completion of the reaction, 3N HCl (20 mL) was added to the reaction mixture to adjust the pH to 3-4. The resulting mixture was extracted with EtOAc (2×50 mL), and the combined organic layers were washed with H2O (2×20mL) and brine (30 mL), and dried (MgSO4). The crude product was purified by flash column chromatography (eluting with hexane/EtOAc, 20:1) to obtain 7 (1.28g, 92% yield) as white powder.

Reference： [1]Lu, Chen; Zhang, Qiang; Chen, Xin [Synthetic Communications, 2016, vol. 46, # 14, p. 1215 - 1222]

6
[ 30060-12-9 ]
[ 1583272-35-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: thionyl chloride; hydrogenchloride / 2 h / Inert atmosphere; Reflux 2: iron; hydrogenchloride / ethanol / 8 h / Inert atmosphere; Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 24 h / 60 °C / Inert atmosphere 4: palladium diacetate; potassium acetate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: sulfuric acid / 6 h / 70 °C 2: acetic acid; tin(ll) chloride / methanol / 5 h / Reflux; Cooling with ice 3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 6 h / 70 °C 4: tetrabutyl-ammonium chloride; triphenylphosphine; sodium acetate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 100 °C

Reference： [1]Lu, Chen; Zhang, Qiang; Chen, Xin [Synthetic Communications, 2016, vol. 46, # 14, p. 1215 - 1222]
[2]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN105541801, 2016, A

7
[ 610-71-9 ]
[ 1583272-35-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: sulfuric acid; nitric acid / 5 h / 100 °C / Inert atmosphere 2: thionyl chloride; hydrogenchloride / 2 h / Inert atmosphere; Reflux 3: iron; hydrogenchloride / ethanol / 8 h / Inert atmosphere; Reflux 4: potassium carbonate / N,N-dimethyl-formamide / 24 h / 60 °C / Inert atmosphere 5: palladium diacetate; potassium acetate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1: sulfuric acid; nitric acid / 5 h / 80 °C 2: sulfuric acid / 6 h / 70 °C 3: acetic acid; tin(ll) chloride / methanol / 5 h / Reflux; Cooling with ice 4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 6 h / 70 °C 5: tetrabutyl-ammonium chloride; triphenylphosphine; sodium acetate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 100 °C

Reference： [1]Lu, Chen; Zhang, Qiang; Chen, Xin [Synthetic Communications, 2016, vol. 46, # 14, p. 1215 - 1222]
[2]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN105541801, 2016, A

8
[ 1215298-17-1 ]
[ 1583272-35-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: iron; hydrogenchloride / ethanol / 8 h / Inert atmosphere; Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 60 °C / Inert atmosphere 3: palladium diacetate; potassium acetate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: acetic acid; tin(ll) chloride / methanol / 5 h / Reflux; Cooling with ice 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 6 h / 70 °C 3: tetrabutyl-ammonium chloride; triphenylphosphine; sodium acetate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 100 °C

Reference： [1]Lu, Chen; Zhang, Qiang; Chen, Xin [Synthetic Communications, 2016, vol. 46, # 14, p. 1215 - 1222]
[2]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN105541801, 2016, A

9
[ 1595849-35-6 ]
[ 1583272-35-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 60 °C / Inert atmosphere 2: palladium diacetate; potassium acetate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 6 h / 70 °C 2: tetrabutyl-ammonium chloride; triphenylphosphine; sodium acetate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 100 °C

Reference： [1]Lu, Chen; Zhang, Qiang; Chen, Xin [Synthetic Communications, 2016, vol. 46, # 14, p. 1215 - 1222]
[2]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN105541801, 2016, A

10
[ 1583272-35-8 ]
[ 1922199-98-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; methylene chloride; sodium hydroxide / N,N-dimethyl-formamide / 20 °C 2: sodium hydroxide / methanol; water

Reference： [1]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN105541801, 2016, A

11
[ 14898-79-4 ]
6-bromo-3-methyl-1H-indole-4-carboxylic acid methyl ester [ No CAS ]
(S)-6-bromo-1-isobutyl-3-methyl-1H-indole-4-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methylene chloride; triethylamine; sodium hydroxide In N,N-dimethyl-formamide at 20℃;	64 Step (6) :( S) -6- bromo-1- (isobutyl) -3-methyl-1-hydrogen - indole-4-carboxylic acidMethyl ester (R) -2- butanol (1.55g, 20.9mmol) and methyl chloride (4.39g, 23.0 mmol) in N, N- dimethylformamide and triethylamine (4.37mL under 31.4 mmol) acylating hydroxyl action, resulting p-toluenesulfonyl ester and then with 6-bromo-3-methyl -1H- indole-4-carboxylate (15mmol) and sodium hydroxide in DMF , and stirred at room temperature overnight to give the product 1.2g (87% yield); Other conditions same as in Example 52, a mixture of 6-bromo-3-methyl-1-hydrogen-indole-4-carboxylate and (R) - isobutanol molar ratio was changed to 1: 4, the resulting product was 92%.

Reference： [1]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN105541801, 2016, A Location in patent: Paragraph 0100

12
[ 1583272-35-8 ]
[ 1826865-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 20 °C 2.1: water; sodium hydroxide / ethanol / 1 h / 60 °C

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN105037360, 2016, B

13
[ 1583272-35-8 ]
[ 1826865-69-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 20 °C 2.1: water; sodium hydroxide / ethanol / 1 h / 60 °C 3.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dimethyl sulfoxide / 20 °C

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN105037360, 2016, B

14
[ 1583272-35-8 ]
[ 1826865-58-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 20 °C 2.1: water; sodium hydroxide / ethanol / 1 h / 60 °C 3.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dimethyl sulfoxide / 20 °C 4.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN105037360, 2016, B

15
[ 137-43-9 ]
[ 1583272-35-8 ]
[ 1826865-67-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 6-bromo-3-methyl-1H-indole-4-carboxylic acid methyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: Cyclopentyl bromide In N,N-dimethyl-formamide at 20℃;	41.1 Step 1 To 6-bromo-3-methyl -1H-indole-4-carboxylic acid methyl ester (l. 0g, 3.94mmol) N the solid, N-dimethyl formamide (25 ml) of the cooling in the 0 °C) solution is added sodium hydride (0.173g, 4 . 33mmol). Stirring for 15 minutes, at this time by adding bromo cyclopentane (0.554 ml, 5 . 90mmol). The reaction is then heated to and maintained at room temperature overnight. To back to the reaction vessel in ice bath and stirring 15 minutes. Shift eliminates the ice-bath and the reaction stirring 1 hour. Removing in a vacuum and about half of the reaction volume of the saturated ammonium chloride solution (200 ml) in. With ethyl ether (2x) extraction and salt water cleaning combined organic matter, drying (MgS04) and concentrated. Using the mobile phase is methanol methylene chloride [...] =40 1 conditions column chromatography purification to obtain the product.

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY - CN105037360, 2016, B Location in patent: Paragraph 0425; 0426; 0427

16
[ 107650-22-6 ]
[ 1583272-35-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.5 h / 0 °C 1.2: 2.5 h / 0 - 20 °C 2.1: zinc(II) iodide; sodium cyanoborohydride / 1,2-dichloro-ethane / 16 h / 20 °C

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

17
[ 1353636-63-1 ]
[ 1583272-35-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; zinc(II) iodide In 1,2-dichloro-ethane at 20℃; for 16h;	General Procedure VII: Preparation of methyl 6-bromo-1-isopropyl-3-methylindoline-4-carboxylate (24a) General procedure: ZnI2 (2.68 g, 13.9 mmol, 1.5 eq) added slowly to a stirred solution of 21a (3.0 g, 9.28 mmol) in 30 mL 1,2-dichloroethane followed by addition of NaCNBH3 (4.38 g, 69.6 mmol, 7.5 eq). The reaction mixture was allowed to stir at RT for 16 h. The progress of the reaction was monitored by TLC and LCMS. The reaction mixture was diluted with water (50 mL) and extracted with CH2Cl2 (3 × 30 mL). The combined organic layers were washed with brine (30 mL) and dried over anhydrous sodium sulfate. Removal of solvent under reduced pressure afforded a crude oil which was purified by SiO2 chromatography using CH2Cl2-hexane to afford 1.2 g (43%) of methyl 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylate (21a′).

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

18
[ 1583272-35-8 ]
[ 2055347-50-5 ]

Yield	Reaction Conditions	Operation in experiment
79.5%	With sodium cyanoborohydride; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 2h; Cooling with ice; Inert atmosphere;	1 Step 1: Compound 5a-1 (2.03 g, 7.42 mmol) and trifluoroacetic acid (4.33 g, 37.98 mmol) in DCE (30 mL) were cooled under an ice bath under argon atmosphere and sodium cyanoborohydride NaCNBH3 (955 mg, 15.2 mmol) was added dropwise, the mixture was stirred at room temperature for 2 hours. LC-MS was followed until the reaction was completed. The reaction solution was poured into the ice water, adjusted to pH 9 with 4N sodium hydroxide solution, extracted with dichloromethane, and the organic layer was dried and concentrated, and purified by combiflash (PE:EA=100:0-90:10) to give the yellow oil compound 7a-1 (1.59 g, 79.5%). MS m/z (ESI): 272 [M+H]+.
	With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 16h;	General Procedure VII: Preparation of methyl 6-bromo-1-isopropyl-3-methylindoline-4-carboxylate (24a) General procedure: TFA (1.5 mL) was added to a solution 21a′ (250 mg, 0.80 mmol) and triethylsilane (280 mg, 2.42 mmol, 3 eq) in CH2Cl2 (8.0 mL). The reaction mixture was allowed to stir at RT for 16 h. The progress of the reaction was monitored by LCMS. The reaction mixture was diluted with CH2Cl2 (30 mL), washed with a saturated aqueous NaHCO3 solution (40 mL) followed by brine and dried over anhydrous sodium sulfate. Removal of solvent afforded 230 mg of methyl 6-bromo-1-isopropyl-3-methylindoline-4-carboxylate (24a).

Reference： [1]Current Patent Assignee: YANGTZE RIVER PHARMACEUTICAL GROUP CO LTD - US2019/300506, 2019, A1 Location in patent: Paragraph 0117
[2]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

19
[ 1583272-35-8 ]
[ 2055347-51-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

20
[ 1583272-35-8 ]
[ 2055347-52-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

21
[ 1583272-35-8 ]
[ 2055347-62-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: trimethylaluminum / toluene; tetrahydrofuran / 18 h

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

22
[ 1583272-35-8 ]
[ 2055347-63-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: trimethylaluminum / toluene; tetrahydrofuran / 18 h

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

23
[ 1583272-35-8 ]
[ 2055347-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 15 h / 90 °C / Inert atmosphere

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

24
[ 1583272-35-8 ]
[ 2055347-67-4 ]
[ 2055347-67-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: trimethylaluminum / toluene; tetrahydrofuran / 18 h 4.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine / dimethyl sulfoxide / 16 h / 20 °C

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

25
[ 1583272-35-8 ]
[ 2055347-73-2 ]
[ 2055347-73-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 15 h / 90 °C / Inert atmosphere 4.1: trimethylaluminum / toluene; tetrahydrofuran / 18 h

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

26
[ 1583272-35-8 ]
[ 2055347-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: trimethylaluminum / toluene; tetrahydrofuran / 18 h 4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 16 h / 90 °C / Inert atmosphere

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

27
[ 1583272-35-8 ]
[ 2055347-77-6 ]
[ 2055347-77-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: trimethylaluminum / toluene; tetrahydrofuran / 18 h 4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 16 h / 90 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

28
[ 1583272-35-8 ]
[ 2055347-78-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 16 h / 90 °C / Inert atmosphere

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

29
[ 1583272-35-8 ]
[ 2055347-79-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 16 h / 90 °C / Inert atmosphere 4.1: lithium hydroxide / water; tetrahydrofuran; methanol / 16 h / 20 °C

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

30
[ 1583272-35-8 ]
[ 2055347-80-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 16 h / 90 °C / Inert atmosphere 4.1: lithium hydroxide / water; tetrahydrofuran; methanol / 16 h / 20 °C 5.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 16 h / 20 °C

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

31
[ 1583272-35-8 ]
[ 2055348-22-4 ]
[ 2055348-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 16 h / 90 °C / Inert atmosphere 4.1: lithium hydroxide / water; tetrahydrofuran; methanol / 16 h / 20 °C 5.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 16 h / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 20 °C

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

32
[ 1583272-35-8 ]
[ 2055347-85-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 16 h / Inert atmosphere

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

33
[ 1583272-35-8 ]
[ 2055347-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 16 h / Inert atmosphere 4.1: trimethylaluminum / toluene

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

34
[ 1583272-35-8 ]
[ 2055347-94-7 ]
[ 2055347-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: acetic acid / dichloromethane / 0.5 h / 20 °C 2.2: 16 h / 20 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 16 h / Inert atmosphere 4.1: trimethylaluminum / toluene 5.1: trifluoroacetic acid / dichloromethane / 20 °C

Reference： [1]Ansari, Amantullah; Satalkar, Sharad; Patil, Varshavekumar; Shete, Amit S.; Kaur, Simranjeet; Gupta, Ashu; Singh, Siddhartha; Raja, Mohd.; Severance, Daniel L.; Bernales, Sebastián; Chakravarty, Sarvajit; Hung, David T.; Pham, Son M.; Herrera, Francisco J.; Rai, Roopa [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222]

35
[ 1583272-35-8 ]
[ 1346575-60-7 ]