1-Benzyl-2,3,7-tribromo-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester → 1-Benzyl-2,3-dibromo-7-cyano-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642466Notes

Reaction equation

HRID 642466 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:25])=[C:8]2[C:15]([Br:16])=[C:14]([Br:17])[N:13]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]2=[C:10](Br)[N:11]=1)=[O:5])[CH3:2].[C:26]([Cu])#[N:27]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:25])=[C:8]2[C:15]([Br:16])=[C:14]([Br:17])[N:13]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]2=[C:10]([C:26]#[N:27])[N:11]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 866173701-Benzyl-2,3,7-tribromo-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterHCID 178418546HCID 178418546, compound

Product 1

HCID 684275281-Benzyl-2,3-dibromo-7-cyano-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Procedure

Prepared in analogy to that of Example 105(a) from 1-benzyl-2,3,7-tribromo-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester and CuCN. The title compound, ESI MS (m/z): 478 (M+H)+.

Sources & evidence

ORD record
ord-55933d09d6a749d5946bcc004fd0ba41
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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