Dimethylformamide → 3,5-dichloro-4-(1H-pyrrolo[2,3-c]pyridin-3-ylcarbonyl)benzonitrile

HRID 2201833Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([C:11]2[C:19]3[C:14](=[CH:15][N:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[O:10])=[C:4]([Cl:20])[CH:3]=1.[CH3:21][N:22](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.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]>[Cl:20][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([Cl:8])[C:5]=1[C:9]([C:11]1[C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:10])[C:21]#[N:22]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of (4-bromo-2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone (100 mg, 0.27 mmol) in dimethylformamide (3 mL) was treated with zinc cyanide (25.2 mg, 0.21 mmol), tris(dibenzylideneacetone)dipalladium (0) (6.21 mg, 0.006 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (5.6 mg, 0.01 mmol) followed by heating at 130° C. for 16 hours. The reaction mixture was diluted with ethyl acetate, filtered over celite, and the filtrate was concentrated under vacuum. The crude compound was purified by LC-MS to afford 3,5-dichloro-4-(1H-pyrrolo[2,3-c]pyridin-3-ylcarbonyl)benzonitrile (2 mg, 2%).

Workup

filtrationfiltered over celite
concentrationthe filtrate was concentrated under vacuum
customThe crude compound was purified by LC-MS

Sources & evidence

ORD record: ord-6a2d006854744bf4b2bd93c71bc61db9
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09364466B2

Reaction notes

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