N-bromobutanimide → 4-Acetoxy-1-benzyl-3-bromo-7-cyano-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642469Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:24][C:25](=[O:27])[CH3:26])=[C:8]2[CH:16]=[CH:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])[CH3:2].C1C(=O)N([Br:35])C(=O)C1>CC#N>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:24][C:25](=[O:27])[CH3:26])=[C:8]2[C:16]([Br:35])=[CH:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-acetoxy-1-benzyl-7-cyano-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (225 mg), NBS (116 mg) in MeCN (3 mL) in a closed vial was heated at 90° C. overnight. Then the solvent was removed, the residue was purified with column to give the desired product (232 mg). The title compound, ESI MS (m/z): 442 (M+H)+.

Workup

customThen the solvent was removed
customthe residue was purified with column

Sources & evidence

ORD record: ord-39ceac0f80ef48af84630b77e02ef5c7
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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