Propargyl bromide → 3-(5-bromomethyl-isoxazol-3-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole

HRID 644070노트

반응식

HRID 644070 반응식
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([CH:19]=[N:20][OH:21])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClN1C(=O)CCC1=O.[CH2:30]([Br:33])[C:31]#[CH:32].C(N(CC)CC)C>ClCCl>[Br:33][CH2:30][C:31]1[O:21][N:20]=[C:19]([C:10]2[C:11]3[C:16](=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:9]=2)[CH:32]=1

참가 물질

6

반응물 4

HCID 7842Propargyl bromideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 860732891-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oxime

생성물 1

HCID 686958133-(5-bromomethyl-isoxazol-3-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole수율 62.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oxime (170 mg, 0.59 mmol) in dichloromethane (5 ml) cooled to 0° C., was added N-chlorosuccinimide (119 mg, 0.89 mmol) and the mixture allowed to warm to room temperature with stirring for 1 h. Propargyl bromide (8 μl, 0.65 mmol) and triethylamine (9 μl, 0.65 mmol) were added and the mixture stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was purified by flash column chromatography eluting with 60-80% (v/v) dichloromethane in n-heptane to afford 3-(5-bromomethyl-isoxazol-3-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole (150 mg, 0.37 mmol) as a yellow solid.

후처리

  1. stirringthe mixture stirred at room temperature for 16 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash column chromatography
  4. washeluting with 60-80% (v/v) dichloromethane in n-heptane

출처 및 근거

ORD 기록
ord-e8b71b51163d404eada7a98bb40cf3f7
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700634B2

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