Potassium trimethylsilanolate → N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d]oxazol-6-yl)cyclopropanesulfonamide

HRID 928984노트

반응식

HRID 928984 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:19]3[C:11](=[CH:12][C:13]4[O:17][CH:16]=[N:15][C:14]=4[C:18]=3[F:20])[N:10]([S:21]([CH:24]3[CH2:26][CH2:25]3)(=[O:23])=[O:22])C2=O)=[C:4]([Cl:28])[CH:3]=1.C[Si](C)(C)[O-].[K+]>C1COCC1>[F:20][C:18]1[C:14]2[N:15]=[CH:16][O:17][C:13]=2[CH:12]=[C:11]([NH:10][S:21]([CH:24]2[CH2:25][CH2:26]2)(=[O:22])=[O:23])[C:19]=1[NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[Cl:28]

참가 물질

4

반응물 2

HCID 23668039Potassium trimethylsilanolateHCID 897053485-(4-bromo-2-chlorophenyl)-7-(cyclopropylsulfonyl)-4-fluoro-5H-imidazo[4',5':4,5]benzo[1, 2-d]oxazol-6(7H)-one

생성물 1

HCID 71667809N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d]oxazol-6-yl)cyclopropanesulfonamide수율 63.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-(4-bromo-2-chlorophenyl)-7-(cyclopropylsulfonyl)-4-fluoro-5H-imidazo[4′,5′:4,5]benzo[1,2-d]oxazol-6(7H)-one (100 mg, 0.21 mmol) in THF (10 mL) was added potassium trimethylsilanolate (40 mg, 0.31 mmol). After stirring at room temperature for 1 h, the reaction was quenched with saturated NH4Cl (aq.). The aqueous layer was extracted with ethyl acetate (10 mL×2). The combined organic phase was washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residual crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate, 5:1-3:1, v/v) and the product was obtained as a white solid (60 mg, 63.4% yield). 1H NMR (400 MHz, CDCl3): δ 8.10 (s, 1H), 7.97 (s, 1H), 7.40 (m, 2H), 7.31-7.26 (m, 1H), 6.81 (s, 1H), 6.40-6.36 (m, 1H), 6.23 (s, 1H), 5.86-5.72 (m, 1H), 5.25-5.13 (m, 2H), 2.85 (d, 2H), 1.30-1.22 (m, 2H), 1.15-1.20 (m, 2H). 8.17 (s, 1H), 7.97 (s, 1H), 7.49 (dd, 1H), 7.35 (s, 1H), 7.26 (dd, 1H), 6.17 (m, 1H), 5.44 (s, 1H), 2.57 (m, 1H), 1.06-1.08 (m, 2H), 1.00-1.01 (m, 2H). MS APCI (+) m/z: 461.7, [M+H].

후처리

  1. customthe reaction was quenched with saturated NH4Cl (aq.)
  2. extractionThe aqueous layer was extracted with ethyl acetate (10 mL×2)
  3. washThe combined organic phase was washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate, 5:1-3:1

출처 및 근거

ORD 기록
ord-c4228e07068d45c097648704d5f82621
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290468B2

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