Sodium Carbonate → HCID 19921656, 화합물

HRID 1463322노트

반응식

HRID 1463322 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=1I.[Si:15]([O:22][CH2:23][CH2:24][CH2:25][C:26]#[C:27][Si:28]([CH3:31])([CH3:30])[CH3:29])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Si:15]([O:22][CH2:23][CH2:24][CH2:25][C:26]1[C:3]2[C:2](=[CH:7][CH:6]=[C:5]([CH2:8][S:9]([NH:12][CH3:13])(=[O:11])=[O:10])[CH:4]=2)[NH:1][C:27]=1[Si:28]([CH3:29])([CH3:30])[CH3:31])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 107584621-(4-Amino-3-iodophenyl)-N-methylmethanesulfonamideHCID 10923628HCID 10923628, 화합물

생성물 1

HCID 19921656HCID 19921656, 화합물수율 88%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a solution of 0.326 g (1.0 mmol, 1.0 equiv.) of 4-amino-3-iodo-N-methylbenzenemethanesulfonamide in 20 mL of dimethylformamide was added 0.541 g (2.0 mmol, 2.0 equiv.) of 1-t-butyldimethylsilyloxy-5-trimethylsilyl-4-pentyne, 0.278 g (1.0 mmol, 1.0 equiv.) of tetrabutylammonium chloride, 0.530 g (5.0 mmol, 5.0 equiv.) of sodium carbonate, 0.0131 g (0.05 mmol, 0.05 equiv.) of triphenylphosphine, and 0.0112 g (0.05 g, 0.05 equiv.) of palladium (II) acetate. The mixture was heated in a 100° C. oil bath for 16 hours. The mixture was cooled to room temperature and the dimethylformamide removed in vacuo. The residue was diluted with 75 mL of ethyl acetate and washed with 25 mL of saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield an oil. The oil was filtered through a plug of silica gel with 25% ethyl acetate in hexane to yield 0.411 g (88%) of 3-(3-t-butyldimethylsilyloxypropyl)-2-trimethylsilyl-N-methyl-1H-indole-5-methanesulfonamide.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customthe dimethylformamide removed in vacuo
  3. additionThe residue was diluted with 75 mL of ethyl acetate
  4. washwashed with 25 mL of saturated aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield an oil
  9. filtrationThe oil was filtered through a plug of silica gel with 25% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-83aca1153c294e43bfa371e1651551b0
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05300506

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