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

HRID 644070ノート

反応式

HRID 644070 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e8b71b51163d404eada7a98bb40cf3f7
出典データセット
uspto-grants-2010_04
特許番号
US07700634B2

反応ノート

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