Dimethylacetamide → 1H-pyrrolo(2,3-b)pyridine-4-carbonitrile

HRID 2282215Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[CH3:11][N:12](C)C(=O)C>[C-]#N.[Zn+2].[C-]#N.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH:8]1[C:4]2[N:5]=[CH:6][CH:7]=[C:2]([C:11]#[N:12])[C:3]=2[CH:10]=[CH:9]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (3.1 g, 20 mmol), zinc cyanide (1.4 g, 12 mmol), zinc (130 mg, 2.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (370 mg, 0.40 mmol), 1,1′-bis(diphenylphosphino)ferrocene (440 mg, 0.80 mmol) and N,N-dimethylacetamide (20 mL) was stirred at 120° C. for 1.5 hr under an argon atmosphere. The reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→100/0), and the obtained solution was concentrated under reduced pressure. The obtained residue was washed with diisopropyl ether to give the title compound (2.60 g, 91%) as a red-brown solid.

Workup

customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→100/0)
concentrationthe obtained solution was concentrated under reduced pressure
washThe obtained residue was washed with diisopropyl ether

Sources & evidence

ORD record: ord-b58a4ae8cf2247c09ec2f047f0b35ea2
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139589B2

Reaction notes

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