Water → 4-(1-Benzyloxy-ethyl)-5-bromo-nicotinonitrile

HRID 712707Notes

Reaction equation

[CH2:1]([O:8][CH:9]([C:11]1[C:16]([Br:17])=[CH:15][N:14]=[CH:13][C:12]=1Br)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cu](C#N)[C:20]#[N:21].O>CN(C=O)C>[CH2:1]([O:8][CH:9]([C:11]1[C:12]([C:20]#[N:21])=[CH:13][N:14]=[CH:15][C:16]=1[Br:17])[CH3:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 4-(1-benzyloxy-ethyl)-3,5-dibromo-pyridine (400 mg, 1.1 mmol) in DMF (5 mL) is added copper cyanide (116 mg, 1.3 mmol). The mixture is heated and stirred at 150° C. for 3 h, then stirred at room temperature for 16 h. H2O is added and the mixture is extracted with EtOAc. The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography provides 225 mg of 4-(1-benzyloxy-ethyl)-5-bromo-nicotinonitrile.

Workup

temperatureThe mixture is heated
stirringstirred at room temperature for 16 h
extractionthe mixture is extracted with EtOAc
concentrationconcentrated
customto give the crude product
customPurification by flash column chromatography

Sources & evidence

ORD record: ord-90839c81f4a34d9db5c80f4d148c479b
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181272B2

Reaction notes

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