Sodium Carbonate → HCID 19921656、化合物

HRID 1647773ノート

反応式

HRID 1647773 の反応式
[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]

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 107584621-(4-Amino-3-iodophenyl)-N-methylmethanesulfonamideHCID 10923628HCID 10923628、化合物

生成物 1

HCID 19921656HCID 19921656、化合物収率 88%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6917c42e690844a3885a3096bc0c5856
出典データセット
uspto-grants-1995_07
特許番号
US05434154

反応ノート

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