Hydrochloric Acid → 1-(1H-Pyrrolo[3,2-c]pyridin-4-yl)ethan-1-one

HRID 2409009Notes

Reaction equation

Cl[C:2]1[C:7]2[CH:8]=[CH:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:16]([O:18]CC)=[CH2:17])CCC.Cl>CN1C(=O)CCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:10]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:16](=[O:18])[CH3:17])[C:7]=2[CH:8]=[CH:9]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 4-chloro-1H-pyrrolo[3,2-c]pyridine (1.0 g, 6.58 mmol), Pd(PPh3)4 (763 mg, 0.66 mmol), and tributyl(1-ethoxyvinyl)stannane (2.61 g, 7.23 mmol) in NMP (20 mL) was stirred under N2 at 140° C. for 18 h. The reaction mixture was poured into aqueous HCl solution (2 N, 150 mL), stirred at RT for 2 h, and washed with DCM (50 mL×3). The aqueous layer was adjusted to pH 8 with NaHCO3 (solid), extracted with EtOAc (50 mL×3), and concentrated under reduced pressure to afford 680 mg (64.6%) of 1-(1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone as yellow solid: MS (ESI) nilz: 161.1 [M+1]+.

Workup

stirringstirred at RT for 2 h
washwashed with DCM (50 mL×3)
extractionextracted with EtOAc (50 mL×3)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f3588d3cfcd1402895e94a06bc8d86cb
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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