tert-Butyl 4-bromo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate → 4-(2-Cyano-5-methoxycarbonyl-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

HRID 1909030Notes

Reaction equation

HRID 1909030 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[CH:13][N:14]=[CH:15][C:16](Br)=[C:11]2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20](=[O:38])[C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=1>>[C:1]([O:5][C:6]([N:8]1[C:12]2=[CH:13][N:14]=[CH:15][C:16]([C:23]3[CH:22]=[C:21]([C:20]([O:19][CH3:18])=[O:38])[CH:26]=[CH:25][C:24]=3[C:27]#[N:28])=[C:11]2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 56592975tert-Butyl 4-bromo-1H-pyrrolo[2,3-c]pyridine-1-carboxylateHCID 56973105HCID 56973105, compound

Product 1

HCID 672864874-(2-Cyano-5-methoxycarbonyl-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

Procedure

Using 4-bromo-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester (synthesized based on US 2005/0090529 A1, p82) (1 mol. eq.) and 4-cyano-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.0 mol. eq.) a starting materials, the reaction was performed using General procedure L (Suzuki) to give 4-(2-cyano-5-methoxycarbonyl-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester. MS(ESI) m/z 378.4 (M+H)+.

Sources & evidence

ORD record
ord-ee6bcc7cc06741f88e4683b870850a2f
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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