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

HRID 2075662ノート

反応式

HRID 2075662 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.CCOC(C)=O.O.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

9

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 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

1q (2.2 g, 5.3 mmol), benzophenone imine (1.1 g, 5.8 mmol), and sodium tert-butoxide (620 mg, 6.5 mmol) were dissolved in toluene (50 mL). Pd2dba3 (98 mg, 0.11 mmol) and BINAP (270 mg, 0.43 mmol) were added, and the reaction was heated to 80° C. for 2 hours. After cooling to room temperature, the mixture was diluted with EtOAc and water, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered, and concentrated to give the desired product, 1r.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-6e4b779b7c1840f3be846d671eaceb7e
出典データセット
uspto-grants-2011_04
特許番号
US07919621B2

反応ノート

読み込み中…