Bromine → 4-(3-bromo-2-{2-[(2R)-2-methylpyrrolidin-1-yl]ethyl}-1-benzofuran-5-yl)benzonitrile

HRID 494848노트

반응식

HRID 494848 반응식
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)=[CH:14][C:12]=2[CH:13]=1.[Br:26]Br.[O-]S([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O>[Br:26][C:13]1[C:12]2[CH:14]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=3)[CH:16]=[CH:17][C:11]=2[O:10][C:9]=1[CH2:8][CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C@H:2]1[CH3:1]

참가 물질

5

반응물 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 9818903Benzonitrile, 4-(2-(2-((2r)-2-methyl-1-pyrrolidinyl)ethyl)-5-benzofuranyl)-

생성물 1

HCID 675337784-(3-bromo-2-{2-[(2R)-2-methylpyrrolidin-1-yl]ethyl}-1-benzofuran-5-yl)benzonitrile수율 97%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매2회

반응 조건

온도
25 °C

실험 절차

The product from Example 1D (2.5 g (5.2 mmol) and trifluoroacetic acid (40 mL) (TFA) were combined and stirred at 25° C. for 10 min. The mixture was slowly treated with a solution of Br2 (450 μL, 7.8 mmol) in TFA (10 mL). The mixture was allowed to stir at 25° C. for 1 h and then treated with saturated aqueous Na2SO3. The mixture was concentrated and redissolved in 50 mL ethyl acetate. The organic phase was washed with 1M NaOH, dried, and concentrated under reduced pressure to provide the title compound (2.1 g, 97% yield). 1HNMR (300 MHz, CD3OD) δ 1.16 (d, 3H, J=6.1 Hz), 1.42 (m, 1H), 1.78 (m, 2H), 1.98 (m, 1H), 2.32 (m, 1H), 2.50 (m, 2H), 3.11 (m, 2H), 3.28 (m, 2H), 7.58-7.70 (m, 3H), 7.82 (m, 4H); MS (ESI) m/e 409 (M+H)+.

후처리

  1. stirringto stir at 25° C. for 1 h
  2. concentrationThe mixture was concentrated
  3. dissolutionredissolved in 50 mL ethyl acetate
  4. washThe organic phase was washed with 1M NaOH
  5. customdried
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cb1fbaea42144b67ac62a68d81fde0e3
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538138B2

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