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

HRID 252513

反応式

HRID 252513 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a3b2adcd5e7a4039b8a70e9d60a9474a
出典データセット
uspto-grants-2011_01
特許番号
US07868037B2

関連ノート

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