Potassium trimethylsilanolate → HCID 89705457, 화합물

HRID 929071노트

반응식

HRID 929071 반응식
[CH2:1]([C:4]1([S:7]([N:10]2[C:14]3=[CH:15][C:16]4[S:20][N:19]=[N:18][C:17]=4[C:21]([F:22])=[C:13]3[N:12]([C:23]3[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=3[F:30])C2=O)(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C[Si](C)(C)[O-].[K+]>C1COCC1>[CH2:1]([C:4]1([S:7]([NH:10][C:14]2[C:13]([NH:12][C:23]3[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=3[F:30])=[C:21]([F:22])[C:17]3[N:18]=[N:19][S:20][C:16]=3[CH:15]=2)(=[O:8])=[O:9])[CH2:5][CH2:6]1)[CH:2]=[CH2:3]

참가 물질

4

반응물 2

HCID 23668039Potassium trimethylsilanolateHCID 89705484HCID 89705484, 화합물

생성물 1

HCID 89705457HCID 89705457, 화합물수율 87.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 7-((1-allylcyclopropyl)sulfonyl)-4-fluoro-5-(2-fluoro-4-iodophenyl)-5H-imidazo[4′,5′:4,5]benzo[1,2-d][1,2,3]thiadiazol-6(7H)-one (60 mg, 0.11 mmol) in THF (5 mL) was added potassium trimethylsilanolate (14 mg, 0.11 mmol). The reaction was stirred at room temperature for 1 h and quenched with saturated NH4Cl (aq.). The aqueous layer was extracted with EA (10 mL×2). The combined organic phase was washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate, 5:1-3:1, v/v) to give the desired product (50 mg, 87.3% yield). 1H NMR (400 MHz, CDCl3): δ 8.24 (s, 1H), 7.65-7.63 (m, 2H), 7.31 (m, 1H), 7.01 (s, 1H), 6.83 (s, 1H), 5.74-5.56 (m, 1H), 5.02 (m, 2H), 2.77-2.71 (m, 1H), 2.12-2.0 (m, 1H), 1.75-1.71 (m, 2H), 1.21-0.97 (m, 2H).

후처리

  1. customquenched with saturated NH4Cl (aq.)
  2. extractionThe aqueous layer was extracted with EA (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 residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate, 5:1-3:1

출처 및 근거

ORD 기록
ord-d194831c1bf84ef1a39ba1fe41e38626
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290468B2

반응 노트

불러오는 중…