Sodium Bicarbonate → Methyl 4-((5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

HRID 1723243노트

반응식

HRID 1723243 반응식
[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[CH:14]=[CH:13]3)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[O:32][CH3:33].[Al].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[CH:14]=[C:13]3[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 5359268AluminumHCID 544874815-(Cyclopentyloxycarbonyl)amino-1-methylindole

생성물 1

HCID 11453373Methyl 4-((5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate수율 45%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A solution of 5-(cyclopentyloxycarbonyl)amino-1-methylindole (AA) (1.3 g.) and methyl 4-bromomethyl-3-methoxybenzoate (B) (1.3 g.) in N,N-dimethylformamide (25 ml.) was stirred and heated at 100° C., under a nitrogen atmosphere, while protecting the reaction vessel from light with aluminum foil, for 24 hours. The cooled mixture was poured onto saturated aqueous sodium bicarbonate solution (300 ml.), extracted with ethyl acetate (3×100 ml.), the combined extracts washed with brine (50 ml.), dried (MgSO4), and evaporated. The product was isolated by flash chromatography on silica gel (3.5 cm. diameter column) to give the title compound (P) (0.98 g., 45%), identical with that obtained in Example 8.

후처리

  1. extractionextracted with ethyl acetate (3×100 ml.)
  2. washthe combined extracts washed with brine (50 ml.)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe product was isolated by flash chromatography on silica gel (3.5 cm. diameter column)

출처 및 근거

ORD 기록
ord-cb24df80163b4d718ff724a9e5540f89
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04859692

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