Water → 3-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carbonitrile

HRID 2206047Notes

Reaction equation

[Br:1][C:2]1[C:6]2[CH:7]([O:14][CH3:15])[NH:8][CH:9]=[C:10]([C:11]([NH2:13])=O)[C:5]=2[N:4]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.O>C1COCC1>[Br:1][C:2]1[C:6]2[CH:7]([O:14][CH3:15])[NH:8][CH:9]=[C:10]([C:11]#[N:13])[C:5]=2[N:4]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxamide (654 mg) in THF (8 mL) was added Burgess reagent (1152 mg at 0° C.), and the mixture was stirred at 0° C. for 2 hr. 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 (ethyl acetate/hexane) to give the title compound (522 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 (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-a0cc20d43b814b6aa622d9b521fa166d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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