Potassium Phosphate, Tribasic → 7,8-Dimethoxy-[10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepin-10-yl][2-methyl-2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methanone

HRID 1830084ノート

反応式

HRID 1830084 の反応式
[CH3:1][O:2][C:3]1[C:4]([O:27][CH3:28])=[CH:5][C:6]2[N:12]([C:13]([C:15]3[CH:20]=[CH:19][C:18](Br)=[C:17]([CH3:22])[CH:16]=3)=[O:14])[CH2:11][C:10]3=[CH:23][CH:24]=[CH:25][N:9]3[CH2:8][C:7]=2[CH:26]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>[CH3:1][O:2][C:3]1[C:4]([O:27][CH3:28])=[CH:5][C:6]2[N:12]([C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[C:30]([F:41])([F:40])[F:29])=[C:17]([CH3:22])[CH:16]=3)=[O:14])[CH2:11][C:10]3=[CH:23][CH:24]=[CH:25][N:9]3[CH2:8][C:7]=2[CH:26]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 219477397,8-dimethoxy-(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(4-bromo-3-methyl-phenyl)-methanone

生成物 1

HCID 219477487,8-Dimethoxy-[10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepin-10-yl][2-methyl-2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methanone収率 87.1%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

The 7,8-dimethoxy-(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(4-bromo-3-methyl-phenyl)-methanone of Step C (1.0 g) was reacted with 2-trifluoromethylphenyl boronic acid (0.645 g, 1.5 equiv.), potassium phosphate (0.964 g, 2.0 equiv.) and a catalytic amount (0.050 g) of tetrakis(triphenylphosphine) palladium(0) in refluxing dioxane (10 mL) under nitrogen for 24 hours. The reaction was then cooled to room temperature, filtered through Celite, and the solvent removed in vacuo. The residue was dissolved in dichloromethane and the solution was washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The crude product so obtained was purified by chromatography on silica gel eluting with 5% ethyl acetate/dichloromethane to provide the title product (1.0 g) as a white crystalline solid, m.p. 187–188° C.

後処理

  1. filtrationfiltered through Celite
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washthe solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product so obtained
  9. customwas purified by chromatography on silica gel eluting with 5% ethyl acetate/dichloromethane

出典と根拠

ORDレコード
ord-94774aded0574596996b96e6d2fb6c56
出典データセット
uspto-grants-2006_06
特許番号
US07064120B2

反応ノート

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