Morpholine → Acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester

HRID 1793209노트

반응식

HRID 1793209 반응식
Br[CH2:2][C:3]([C:5]1[O:6][C:7]2[C:13]([CH3:14])=[C:12]([CH3:15])[C:11]([O:16][C:17](=[O:19])[CH3:18])=[CH:10][C:8]=2[CH:9]=1)=[O:4].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:15][C:12]1[C:11]([O:16][C:17](=[O:19])[CH3:18])=[CH:10][C:8]2[CH:9]=[C:5]([C:3](=[O:4])[CH2:2][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[O:6][C:7]=2[C:13]=1[CH3:14]

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 101719982-Bromo-1-(5-acetoxy-6,7-dimethyl-benzofuran-2-yl)-ethanone

생성물 1

HCID 10236780Acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester수율 89.8%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of 2-bromo-1-(5-acetoxy-6,7-dimethyl-benzofuran-2-yl)-ethanone (47 mg) from Example 16, morpholine (15 mg), and potassium carbonate (25 mg) in acetone (10 mL) was stirred at room temperature for 30 min. It was then evaporated to dryness, and the residue was purified by silica gel column eluting with 5% MeOH in DCM to give 43 mg of acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester as an oil. Conversion into the HCl salt gave a yellow solid. 1H NMR (CDCl3, 300 MHz) δ: 7.60 (s, 1H), 7.20 (s, 1H), 3.78(s+t, 6H), 2.64(m, 4H), 2.50(s, 3H), 2.40(s, 3H), 2.20(s, 3H) ppm. 13C NMR (CD3OD, 75 MHz) (as HCl salt) δ: 180.94, 170.31, 153.65, 150.33, 147.19, 131.94, 124.33, 122.34, 116.04, 113.59, 63.74, 60.89, 53.28, 19.64, 12.18, 12.22 ppm. M/S 332 (M+H+).

후처리

  1. customIt was then evaporated to dryness
  2. customthe residue was purified by silica gel column
  3. washeluting with 5% MeOH in DCM

출처 및 근거

ORD 기록
ord-b060b3d71c424ba2bba7ef8e1ba232ce
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07078541B2

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