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

HRID 1506517노트

반응식

HRID 1506517 반응식
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]

참가 물질

5

반응물 2

HCID 58374164Methyl 4-iodo-3-phenylisothiazole-5-carboxylateHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 67169144Methyl 4-cyano-3-phenylisothiazole-5-carboxylate수율 85%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-99cfaceee9b5403e9a2f9a2f56a273fd
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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