Water → 1-benzenesulfonyl-4-trifluoromethyl-1H-indole

HRID 913487노트

반응식

HRID 913487 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:14]1([S:20]([N:7]2[C:8]3[C:4](=[C:3]([C:2]([F:1])([F:12])[F:13])[CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 198037034-(Trifluoromethyl)-1H-indole

생성물 1

HCID 578003941-benzenesulfonyl-4-trifluoromethyl-1H-indole수율 82%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

실험 절차

To a solution of 4-(trifluoromethyl)-1H-indole (0.535 g, 2.89 mmol; step A above), tetrabutylammonium bromide (0.097 g, 0.30 mmol) and benzenesulfonyl chloride (0.44 mL, 3.5 mmol) in PhMe (5 mL) at rt was added 50 wt % NaOH (3 mL) and H2O (2 mL). The mixture was stirred 30 min, partitioned between Et2O/H2O and the layers were separated. The organic layer was washed (H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.771 g of the title compound as a thick, pale yellow oil: 1H NMR (300 MHz, methanol-d4) δ 8.25 (d, J=8.3 Hz, 1H), 8.00-7.94 (m, 2H), 7.88 (d, J=3.8 Hz, 1H), 7.65-7.58 (m, 1H), 7.57-7.41 (m, 4H), 6.87 (br. s, 1H).

후처리

  1. custompartitioned between Et2O/H2O
  2. customthe layers were separated
  3. washThe organic layer was washed (H2O, brine)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-94e027388eab45089c086e00acfb0296
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026262B2

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