Methyl 4-iodo-3-phenylisothiazole-5-carboxylate → Methyl 4-cyano-3-phenylisothiazole-5-carboxylate

HRID 1506517Notes

Reaction equation

I[C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[Cu](C#N)[C:18]#[N:19]>CN1C(=O)CCC1.CCOC(C)=O>[C:18]([C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8])#[N:19]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 4-iodo-3-phenylisothiazole-5-carboxylate (Preparation 103D, 600 mg, 1.738 mmol) in NMP (2 mL) was added copper cyanide (311 mg, 3.48 mmol). The resulting mixture was heated at 100° C. in a microwave reactor for 45 min. The reaction mixture was diluted with EtOAc (40 mL), filtered, washed with water (2×20 mL), brine (10 mL) and concentrated. Flash chromatography gave methyl 4-cyano-3-phenylisothiazole-5-carboxylate (360 mg, 1.474 mmol, 85% yield) as a white solid. The compound had an LC/MS M+1=245.1.

Workup

filtrationfiltered
washwashed with water (2×20 mL), brine (10 mL)
concentrationconcentrated

Sources & evidence

ORD record: ord-99cfaceee9b5403e9a2f9a2f56a273fd
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216972B2

Reaction notes

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