Benzonitrile, 4-bromo- → HCID 178461988, 화합물

HRID 46146

반응식

HRID 46146 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 178461988HCID 178461988, 화합물

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
95 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-186e9403d5944feca041a124aeb48779
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541592B2

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