1,4-Dioxane → 1,3Dioxol-5-yl-2-(4-imidazol-1-yl-phenyl)-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

HRID 988332

反応式

HRID 988332 の反応式
O1C2C=CC([CH:10]3[C:14]4[NH:15][C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[C:22](=[O:23])[C:13]=4[CH2:12][NH:11]3)=CC=2OC1.Br[C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)=[CH:27][CH:26]=1.C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.CC([O-])(C)C.[Na+].[O:63]1[CH2:68]C[O:66][CH2:65][CH2:64]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]>[O:63]1[C:64]([CH:12]2[C:13]3[C:22](=[O:23])[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[NH:15][C:14]=3[CH2:10][N:11]2[C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH:35]=[CH:34][N:33]=[CH:32]3)=[CH:27][CH:26]=2)=[CH:65][O:66][CH2:68]1

参加物

7

反応物 5

HCID 312751,4-DioxaneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27356041-(4-Bromophenyl)imidazoleHCID 108921213-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrrolo[3,4-b]quinolin-9-oneHCID 23676156Sodium t-butoxide

生成物 1

HCID 867592211,3Dioxol-5-yl-2-(4-imidazol-1-yl-phenyl)-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

3-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrrolo[3,4-b]quinolin-9-one (30.6 mg, 0.1 mmol), 1-(4-bromo-phenyl)-1H-imidazole (22.3 mg, 0.1 mmol), Pd2dba3 (4.6 mg, 0.005 mmol), biphenyl-2-yl-di-tert-butyl-phosphane 3.0 mg, 0.01 mmol) and NaOtBu (14 mg, 0.14 mmol) were stirred in 1,4-dioxane (0.6 mL) at 89° C. for 17 hours. Purification by preparative TLC (5% CH3OH/CH2Cl2) yielded the title product as yellow powder.

後処理

  1. customPurification by preparative TLC (5% CH3OH/CH2Cl2)

出典と根拠

ORDレコード
ord-40c5ab01addc4ce28732d453c29abdb5
出典データセット
uspto-grants-2003_10
特許番号
US06635638B2

関連ノート

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