Methyl 4-(bromomethyl)-3-methoxybenzoate → HCID 19870596, 화합물

HRID 330193노트

반응식

HRID 330193 반응식
[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]

참가 물질

4

반응물 2

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate2회HCID 54136909HCID 54136909, 화합물

생성물 1

HCID 19870596HCID 19870596, 화합물수율 30%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-63c9d07fe3314235ab25a0de18fc3272
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04894386

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