Chlorosuccinimide → 4-Acetoxy-3-chloro-7-cyano-1-(4-fluoro-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642458Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:25][C:26](=[O:28])[CH3:27])=[C:8]2[CH:16]=[CH:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])[CH3:2].C1C(=O)N([Cl:36])C(=O)C1>CC#N>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:25][C:26](=[O:28])[CH3:27])=[C:8]2[C:16]([Cl:36])=[CH:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[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-7-cyano-1-(4-fluoro-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (103 mg), NCS (38 mg) in MeCN (2 mL) in a closed vial was heated at 90° C. for 1 h. Then the solvent was removed, the residue was purified with column to give the desired product (67 mg). The title compound, ESI MS (m/z): 416 (M+H)+.

Workup

customThen the solvent was removed
customthe residue was purified with column

Sources & evidence

ORD record: ord-c78cc4d2442d42919c3068ba96cf84a2
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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