Sodium hydride → (1R*,2S*)-2-(3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)spiro[cyclo-propane-1,3'-indolin]-2'-one

HRID 1466241노트

반응식

HRID 1466241 반응식
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[I:9][C:10]1[C:18]2[C:13](=[CH:14][C:15](/[CH:19]=[C:20]3/[C:21](=[O:29])[NH:22][C:23]4[C:28]/3=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:16][CH:17]=2)[N:12]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[N:11]=1>CN(C=O)C>[I:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([C@H:19]3[C@@:20]4([C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[NH:22][C:21]4=[O:29])[CH2:2]3)=[CH:16][CH:17]=2)[N:12]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:36])([CH3:35])[CH3:37])[N:11]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 58486274(E)-3-((3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-2-one

생성물 1

HCID 58486328(1R*,2S*)-2-(3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)spiro[cyclo-propane-1,3'-indolin]-2'-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of trimethylsulfoxonium iodide (1.89 g, 8.6 mmol) in anhydrous DMF (40 mL) was added sodium hydride (60% dispersion in oil) (1.03 g, 25.8 mmol) at 0° C. The mixture was stirred for 15 min after which time (E)-3-((3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-2-one (2.2 g, 4.3 mmol) was added. The solution was stirred overnight at rt. The reaction was quenched with sat. NH4Cl solution (50 mL), extracted with EtOAc (4×100 mL), dried over MgSO4 and concentrated to dryness. The title compound was isolated by silica gel chromatography (CH2Cl2/MeOH 98:2) as a yellow solid (1.5 g, 66%). 1H NMR (400 MHz, CDCl3) δ 7.46 (s, 1H), 7.39 (d, 1H J=8.3 Hz), 7.09 (t, 1H, J=7.5 Hz), 7.04 (d, 1H, J=8.0 Hz), 6.92 (d, 1H, J=7.8 Hz), 6.61 (t, 1H, J=8.0 Hz), 5.90 (d, 1H, 8.0 Hz), 5.70 (s, 2H), 3.57-3.53 (m, 2H), 3.49-3.44 (m, 1H), 2.31-2.28 (m, 1H), 2.12-2.09 (m, 1H), 0.89-0.84 (m, 2H), −0.05 (s, 9H); MS ESI 532.1 [M+H]+, calcd for [C23H26IN3O2Si+H]+ 532.4.

후처리

  1. additionwas added
  2. customThe reaction was quenched with sat. NH4Cl solution (50 mL)
  3. extractionextracted with EtOAc (4×100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-53cf1d97acf04bb0a00ab3a5453f738c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999968B2

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