Water → 1H-Pyrrolo[3,2-c]pyridine-4-carbonitrile

HRID 2409008Notes

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.O.[CH3:12][N:13]1C(=O)CCC1>[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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[Zn]>[NH:10]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:12]#[N:13])[C:7]=2[CH:8]=[CH:9]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-chloro-1H-pyrrolo[3,2-c]pyridine (500 mg, 3.28 mmol), zinc cyanide (422 mg, 3.61 mmol), Pd2(dba)3 (600 mg, 0.656 mmol), dppf (729 mg, 1.312 mmol), and Zn powder (21 mg, 0.328 mmol) in NMP (30 mL) under nitrogen was stirred at 120° C. for 18 h. The reaction mixture was cooled, poured into water (150 mL), extracted with DCM (3×50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The crude residue was purified by SiO2 chromatography eluting with petroleum ether:EtOAc (1:1) as eluting solvents to afford 1H-pyrrolo[3,2-c]pyridine-4-carbonitrile as a white solid (150 mg, 32%). MS (ESI) m/z: 144.3 [M+1]+.

Workup

temperatureThe reaction mixture was cooled
extractionextracted with DCM (3×50 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude residue was purified by SiO2 chromatography
washeluting with petroleum ether:EtOAc (1:1)
washas eluting solvents

Sources & evidence

ORD record: ord-17452629810a4ce88190cdd652730f6d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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