Water → 4-(7-cyano-1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)thiophene-2-carboxamide

HRID 2206049Notes

Reaction equation

[C:1]([C:3]1[C:4]2[N:13]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:12]=[C:11]([C:19]3[CH:20]=[C:21]([C:24]([NH2:26])=[O:25])[S:22][CH:23]=3)[C:5]=2[C:6]([O:9]C)=[N:7][CH:8]=1)#[N:2].[I-].[Na+].Cl[Si](C)(C)C.O>C(#N)C>[C:1]([C:3]1[C:4]2[N:13]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:12]=[C:11]([C:19]3[CH:20]=[C:21]([C:24]([NH2:26])=[O:25])[S:22][CH:23]=3)[C:5]=2[C:6](=[O:9])[NH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(7-cyano-1-cyclopentyl-4-methoxy-1H-pyrrolo[3,2-c]pyridin-3-yl)thiophene-2-carboxamide (310 mg) in acetonitrile (40 mL) were added sodium iodide (254 mg) and chloro(trimethyl)silane (536 mL), and the mixture was stirred at 80° C. for 30 min. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (143 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record: ord-c80e76e449964ca490149c29696b550c
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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