Chlorosulfonyl isocyanate → 6-methoxy-2-methyl-1H-indole-3-carbonitrile

HRID 502139

반응식

HRID 502139 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH3:12])[NH:9]2)=[CH:5][CH:4]=1.ClS([N:17]=[C:18]=O)(=O)=O.C([O-])(O)=O.[Na+]>C(#N)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:18]#[N:17])=[C:8]([CH3:12])[NH:9]2)=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 108447096-methoxy-2-methyl-1H-indole

생성물 1

HCID 139046406-methoxy-2-methyl-1H-indole-3-carbonitrile수율 81%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매2회

실험 절차

To a solution of 6-methoxy-2-methyl-1H-indole (3.9 g, 24 mmol) in acetonitrile (200 mL) and DMF (20 mL) is added dropwise a solution of ClSO2NCO (4 mL, 1.3 eq.) in acetonitrile (31 mL) at 0° C. After the addition, the mixture is stirred at room temperature for 3 h. Then it is poured into ice water and saturated NaHCO3 is added to it until it becomes basic. The aqueous phase is extracted with CH2Cl2 and then evaporated. The residue is purified with flash column chromatography on silica gel using EtOAc/petroleum ether (1/5) as eluent to yield 81% of 6-methoxy-2-methyl-1H-indole-3-carbonitrile.

후처리

  1. additionAfter the addition
  2. additionis added to it until it
  3. extractionThe aqueous phase is extracted with CH2Cl2
  4. customevaporated
  5. customThe residue is purified with flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-0aec329a041b43c0bd4bedc4b9fe0881
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772271B2

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