Benzoyl chloride → HCID 9797761、化合物

HRID 367372ノート

反応式

HRID 367372 の反応式
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]1[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH:25]=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([F:10])=[CH:19][CH:18]=2)[C:14]([C:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH:25]=2)=[CH:15]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 149732095-fluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

生成物 1

HCID 9797761HCID 9797761、化合物収率 39%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Benzoyl chloride (33.3 mg, 0.24 mmol) was added to a solution of 5-fluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)indole (Example 4b, 49.6 mg, 0.215 mmol), triethylamine (0.15 mL, 1.1 mmol) and DMAP (5 mg) in dichloromethane (2 mL). The mixture was stirred at room temperature prior to quenching with water and extraction into dichloromethane. The organic layer was washed with brine and dried over sodium sulfate. Purification by flash chromatography (silica gel, 2M methanolic ammonia in chloroform) yielded 1-benzoyl-5-fluoro-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)indole (27.8 mg, 39%, HRMS-FAB+ for C21H20N2OF calculated MH+ : 335.15598; found: 335.15457).

後処理

  1. customto quenching with water and extraction into dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customPurification by flash chromatography (silica gel, 2M methanolic ammonia in chloroform)

出典と根拠

ORDレコード
ord-f4c6370d1b644e638da2e3eb9a5342df
出典データセット
uspto-grants-2000_10
特許番号
US06133287

反応ノート

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