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

HRID 1357280노트

반응식

HRID 1357280 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-e97e2d23b853455bbd15030004bb30d4
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06589970B2

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