Triethylamine → 3-Butyl-benzofuran-2-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide

HRID 1357280ノート

反応式

HRID 1357280 の反応式
[CH2:1]([C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14](Cl)=[O:15])[CH2:2][CH2:3][CH3:4].[Br:17][C:18]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22]([CH2:30][NH:31][CH3:32])=[CH:23]2.C(N(CC)CC)C>C(Cl)Cl>[Br:17][C:18]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22]([CH2:30][N:31]([CH3:32])[C:14]([C:6]1[O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=1[CH2:1][CH2:2][CH2:3][CH3:4])=[O:15])=[CH:23]2

参加物

5

反応物 3

HCID 8471TriethylamineHCID 18505315(5-Bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amineHCID 185053603-Butyl-benzofuran-2-carbonyl chloride

生成物 1

HCID 865873943-Butyl-benzofuran-2-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 3-butyl-benzofuran-2-carbonyl chloride (9.0 mmol), prepared in the previous step, in 50 mL of methylene chloride was added under nitrogen dropwise over 2 h to a solution of (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amine (2.52 g, 9.0 mmol), prepared in step 7 of Example 36, and triethylamine (1.26 mmol, 9.0 mmol) in 250 mL of methylene chloride at room temperature. After the addition the reaction was stirred at room temperature overnight. The reaction was extracted with 1 N HCl, 5% NaHCO3, dried (MgSO4) and the solvent removed under reduced pressure to 4.13 g of a residue. Purification of the residue on 500 g of silica gel (230-400 mesh) using 90% hexane-methylene chloride to 5% EtOAc-methylene chloride as the eluents gave 3-butyl-benzofuran-2-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide as a clear oil, MS m/z: 480 [M+H]+.

後処理

  1. additionAfter the addition the reaction
  2. extractionThe reaction was extracted with 1 N HCl, 5% NaHCO3
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure to 4.13 g of a residue
  5. customPurification of the residue on 500 g of silica gel (230-400 mesh)

出典と根拠

ORDレコード
ord-e97e2d23b853455bbd15030004bb30d4
出典データセット
uspto-grants-2003_07
特許番号
US06589970B2

反応ノート

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