Benzophenone imine → 4-{3-[2-(Benzhydrylidene-amino)-4-chloro-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

HRID 2075674ノート

反応式

HRID 2075674 の反応式
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]#[N:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1.[C:28](=[NH:41])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:28](=[N:41][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]#[N:27])[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[CH:17]=[CH:18][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

7

反応物 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 866138254-[3-(2,4-Dichloro-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

生成物 1

HCID 866138264-{3-[2-(Benzhydrylidene-amino)-4-chloro-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

試薬・触媒・溶媒 2

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

反応条件

温度
80 °C

実験手順

3b (1.0 g, 2.4 mmol), benzophenone imine (0.4 mL, 2.4 mmol), sodium tert-butoxide (350 mg, 3.6 mmol), BINAP (150 mg, 0.27 mmol), and Pd2dba3 (55 mg, 0.06 mmol) were dissolved in toluene (10 mL) and degassed for 10 minutes with N2. The reaction was then sealed and heated to 80° C. for 2 hours. After cooling to room temperature, the reaction was diluted with EtOAc and brine, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (30% EtOAc in hexanes) to give the desired product, 3c.

後処理

  1. customdegassed for 10 minutes with N2
  2. customThe reaction was then sealed
  3. temperatureAfter cooling to room temperature
  4. additionthe reaction was diluted with EtOAc and brine
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue was purified by silica gel chromatography (30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-da2fb24c58244bea9e267c045b491961
出典データセット
uspto-grants-2011_04
特許番号
US07919621B2

反応ノート

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