Methyl 4-(bromomethyl)-3-methoxybenzoate → HCID 19870596、化合物

HRID 330193ノート

反応式

HRID 330193 の反応式
[CH2:1]([NH:5][C:6](=[O:18])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]=[CH:11]2)[CH2:2][CH2:3][CH3:4].Br[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32]>CN(C)C=O>[CH2:1]([NH:5][C:6]([CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]=[C:11]2[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32])=[O:18])[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate2 回HCID 54136909HCID 54136909、化合物

生成物 1

HCID 19870596HCID 19870596、化合物収率 30%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of N-butyl-1-methylindole-5-acetamide (0.46 g) and methyl 4-bromomethyl-3-methoxybenzoate (0.49 g) in dimethylformamide (10 ml) was heated at 80° under a nitrogen atmosphere for 18 hr. Additional methyl 4-bromomethyl-3-methoxybenzoate (0.49 g) was added to the reaction and stirring was continued for 18 hr at 80°. The dimethylformamide was evaporated: and the oily residue was purified by flash chromatography, eluting with 1:1 ethyl acetate:hexane to give methyl 4-(5-butylcarbamoylmethyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate (0.23 g, 30%) as a white solid; NMR (250 MHz, CDCl3): 0.84(t, 3H, N(CH2)CH3), 1.35-1.16(m, 4H, NCH2 (CH2)2), 3.13(q, 2H, NCH2), 3.65(s, 2H, ArCH2CO), 3.75(s, 3H, NCH3), 3.90(s, 3H, OCH3), 3.94(s, 3H, OCH3), 4.09(s, 2H, ArCH2Ar'), 5.34(br, 1H, NH).

後処理

  1. customThe dimethylformamide was evaporated
  2. customthe oily residue was purified by flash chromatography
  3. washeluting with 1:1 ethyl acetate

出典と根拠

ORDレコード
ord-63c9d07fe3314235ab25a0de18fc3272
出典データセット
uspto-grants-1990_01
特許番号
US04894386

反応ノート

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