Triethylamine → HCID 86699758、化合物

HRID 515193ノート

反応式

HRID 515193 の反応式
[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:5]([C:6]([OH:8])=O)=[C:4]([F:13])[CH:3]=1.C(Cl)(=O)C(Cl)=O.[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.C(N(CC)CC)C>ClCCl.O1CCCC1.CN(C)C=O>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:5]([C:6]([NH:26][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([Cl:20])=[CH:22][CH:23]=2)=[O:8])=[C:4]([F:13])[CH:3]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 660364-ChlorobenzylamineHCID 73554900HCID 73554900、化合物

生成物 1

HCID 86699758HCID 86699758、化合物収率 75.2%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution 4-bromo-2-fluoro-6-methoxy-benzoic acid (2.5 g, 10.0 mmol) in dichloromethane (30 ml) is added oxalyl chloride (1.04 ml, 12.0 mmol) added drop wise at 0° C. followed by addition of a catalytic amount of dimethylformamide. The mixture is stirred at the same temperature for 2 h. The solution is added via a cannula to a mixture of 4-chloro benzyl amine (1.7 g, 12.0 mmol) and triethyl amine (4.2 ml, 30.0 mmol) in dry tetrahydrofuran (50 ml) at 0° C. After stirring at room temperature for 16 h the mixture is diluted with dichloromethane (50 ml) and washed with water (50 ml), brine (50 ml), dried over sodium sulfate and evaporated in vacuo. The crude product is purified by column chromatography (silica gel, 5% ethyl acetate/dichloromethane) to obtain 4-bromo-N-[(4-chlorophenyl)-methyl]-2-fluoro-6-methoxy-benzamide (2.8 g, 7.52 mmol, 74%).

後処理

  1. additionadded drop wise at 0° C.
  2. stirringAfter stirring at room temperature for 16 h the mixture
  3. washwashed with water (50 ml), brine (50 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe crude product is purified by column chromatography (silica gel, 5% ethyl acetate/dichloromethane)

出典と根拠

ORDレコード
ord-356a8412f95845ffa6fa99d988fb1729
出典データセット
uspto-grants-2015_08
特許番号
US09108936B2

反応ノート

読み込み中…