Potassium Hydroxide → N-[4-(6,7,8,9-Tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-ylamino)-phenyl]-benzamide

HRID 533721

反応式

HRID 533721 の反応式
Cl[C:2]1[C:10]2[C:9]3[CH2:11][NH:12][CH2:13][CH2:14][C:8]=3[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[OH-].[K+]>C(O)(C)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:5]1[C:6]2[NH:7][C:8]3[CH2:14][CH2:13][NH:12][CH2:11][C:9]=3[C:10]=2[C:2]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)=[CH:3][CH:4]=1

参加物

7

反応物 4

HCID 14797Potassium HydroxideHCID 87196Benzamide, N-(4-aminophenyl)-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 666779724-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrole

生成物 1

HCID 46843080N-[4-(6,7,8,9-Tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-ylamino)-phenyl]-benzamide収率 37.4%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6386tert-Butanol溶媒

反応条件

温度
100 °C

実験手順

4-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (500 mg, 1.78 mmol), N-(4-Amino-phenyl)-benzamide (454 mg, 2.14 mmol), Pd(OAc)2 (20 mg, 0.09 mmol), X-Phos (85 mg, 0.18 mmol), and KOH (300 mg, 5.35 mmol) were dissolved in tert-butanol (9.0 mL), and stirred overnight at 100° C. The reaction mixture was concentrated, and then suspended in EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 1 (255 mg, 37% yield) as a tan solid. LC-MS (M+H=384, obsd.=384).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with EtOAc/H2O
  4. customdried under vacuum

出典と根拠

ORDレコード
ord-3499e09f59414261905778bb3ef10ebb
出典データセット
uspto-grants-2014_10
特許番号
US08853391B2

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