Water → 2-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-trifluoromethyl-1H-indole-5-carbonitrile

HRID 351104노트

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HRID 351104 반응식
[C:1]([C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([NH:13]S(C)(=O)=O)=[C:5](I)[CH:4]=1)#[N:2].[C:19]([Si:23]([O:26][C:27]([CH3:31])([CH3:30])[C:28]#[CH:29])([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20].CCN(CC)CC.O>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:19]([Si:23]([CH3:25])([CH3:24])[O:26][C:27]([C:28]1[NH:13][C:6]2[C:5]([CH:29]=1)=[CH:4][C:3]([C:1]#[N:2])=[C:8]([C:9]([F:12])([F:11])[F:10])[CH:7]=2)([CH3:30])[CH3:31])([CH3:22])([CH3:21])[CH3:20]

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 11084826Silane, (1,1-dimethylethyl)[(1,1-dimethyl-2-propynyl)oxy]dimethyl-HCID 21091191N-(4-Cyano-2-iodo-5-(trifluoromethyl)phenyl)methanesulfonamide

생성물 1

HCID 210911842-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-trifluoromethyl-1H-indole-5-carbonitrile수율 16%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

N-(4-Cyano-2-iodo-5-trifluoromethyl-phenyl)-methanesulfonamide (1.95 g, 5.0 mmol), tert-Butyl-(1,1-dimethyl-prop-2-ynyloxy)-dimethyl-silane (992 mg, 5.0 mmol), PdCl2(PPh3)2, (175 mg, 0.25 mmol), CuI (95 mg, 0.5 mmol), NEt3 (1.4 mL, 10.0 mmol), was mixed in DMF (15 mL) and stirred at room temperature for 16 hours. Water was added and the mixture was extracted twice with ethyl acetate. The organic layers were washed with 10% LiCl solution, dried over magnesium sulfate, filtered, evaporated to a brown oil. The brown oil was purified by column chromatography eluting with 1, 3, and 10% ethyl acetate/hexanes. The product was obtained as a white solid (306 mg, 16%). 1H NMR (CDCl3) δ 8.75 (s, 1H), 7.92 S, 1H), 7.67 (s, 1H), 6.27 (d, J=1.2 Hz, 1H), 1.58 (s, 6H), 0.85 (s, 9H), 0.3 (s, 6H). MS (m/z): 405 (MNa+), 381 (MH−).

후처리

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe organic layers were washed with 10% LiCl solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to a brown oil
  6. customThe brown oil was purified by column chromatography
  7. washeluting with 1, 3, and 10% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-bf522c38f7ab4b769fbb75a1a8b8485b
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183309B2

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