Water → 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile

HRID 2080012Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.O.C(OCC)(=O)C.[CH3:18][N:19]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.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:8]1[C:5]2=[N:6][CH:7]=[C:2]([C:18]#[N:19])[CH:3]=[C:4]2[CH:10]=[CH:9]1

Participants

Conditions

Temperature: 110 °C

Procedure

5-Bromo-1H-pyrrolo[2,3-b]pyridine described in Preparation Example R-5 (90 mg, 0.46 mmol), zinc cyanide (80 mg, 0.69 mmol) and tetrakis(triphenylphosphine)palladium(0) (53 mg, 46 μmol) were dissolved in N-methyl-2-pyrrolidinone (2 mL), and the mixture was stirred for 4.5 hours at 110° C. under nitrogen atmosphere. The reaction mixture was cooled to room temperature, water and ethyl acetate were added to the reaction mixture, the organic layer was partitioned, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), and the title compound (48 mg, 0.34 mmol, 73%) was obtained as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe organic layer was partitioned
washthe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated in vacuo
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-d9c699f3a85f4143b2b23a29a00dfbc9
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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