Benzonitrile, 4-bromo- → HCID 178461988、化合物

HRID 46146

反応式

HRID 46146 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([NH:10][C:11]1[S:12][CH:13]([CH3:17])[C:14](=[O:16])[N:15]=1)[CH3:9].Br[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([NH:10][C:11]1[S:12][C:13]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)([CH3:17])[C:14](=[O:16])[N:15]=1)[CH3:9]

参加物

7

反応物 4

HCID 12162Benzonitrile, 4-bromo-HCID 634876Binap, (A+-)-HCID 2724254Sodium bis(trimethylsilyl)amideHCID 178435110HCID 178435110、化合物

生成物 1

HCID 178461988HCID 178461988、化合物

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

To a mixture of 2-((S)-1-(2-fluorophenyl)ethylamino)-5-methylthiazol-4(5H)-one (0.0500 g, 0.198 mmol), 4-bromobenzonitrile (Aldrich, 0.0721 g, 0.396 mmol), Pd2(dba)3 (Aldrich, 0.0127 g, 0.0139 mmol), 2-(diphenylphosphino)-1-(2-(diphenylphosphino)naphthalen-1-yl)naphthalene (Strem, 0.0123 g, 0.0198 mmol), and NaN(TMS)2 (Aldrich, 0.0727 g, 0.396 mmol) was added toluene (2 mL) in a dry box. The mixture was gradually heated to 95° C. and stirred overnight. The reaction was cooled to ambient temp. and quenched with NH4Cl (5 mL). The reaction mixture was extract with EtOAc. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography. MS: 354 (M+1)

後処理

  1. temperatureThe reaction was cooled to ambient temp.
  2. customquenched with NH4Cl (5 mL)
  3. extractionThe reaction mixture was extract with EtOAc
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-186e9403d5944feca041a124aeb48779
出典データセット
uspto-grants-2013_09
特許番号
US08541592B2

関連ノート

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