Trifluoroacetic acid → 1-[4-(2-Bromethoxy)benzoyl]-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

HRID 2119504노트

반응식

HRID 2119504 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)=[CH:4][CH:3]=1.[Br:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([CH:37]=O)=[O:36])=[CH:31][CH:30]=1.FC(F)(F)C(O)=O>>[Br:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([CH:37]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:36])=[CH:31][CH:30]=1

참가 물질

4

반응물 3

HCID 6422Trifluoroacetic acidHCID 23440827HCID 23440827, 화합물HCID 23440828(4-Fluorophenyl){2-[3-(phenylmethoxy)phenyl]ethyl}amine

생성물 1

HCID 234408451-[4-(2-Bromethoxy)benzoyl]-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline수율 78.4%

실험 절차

To a solution of (4-fluorophenyl){2-[3-(phenylmethoxy)phenyl]ethyl}amine (0.643 g, 2.0 mmol) and [4-(2-bromoethoxy)phenyl]glyoxal (0.617 g, 2.4 mmol) was added trifluoroacetic acid (0.342 g, 3.0 mmol). The reaction stirred at room temperature for 4 hours. The reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated, and purified by column chromatography (SiO2, 20% ethyl acetate/hexane) to provide the title compound (0.879 g, 78% yield): 1H NMR (CDCl3) 8.00 (d, 2H), 7.40 (m, 4H), 7.18 (m, 1H), 7.07 (d, 1H), 6.79-6.92 (m, 8H), 5.85 (s, 1H), 5.02 (s, 2H), 4.33 (t, 2H), 3.71 (m, 1H), 3.64 (t, 2H), 3.47 (m, 1H), 3.07 (m, 1H), 2.87 (m, 11H); ES−MS (m/z) 560 [M+H]+.

후처리

  1. customThe reaction was quenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (SiO2, 20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-89a94c4d58b2492784141d3b3278da2b
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06686351B2

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