Potassium Phosphate, Tribasic → N-[4-({3-Cyclopropyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide

HRID 2192176ノート

反応式

HRID 2192176 の反応式
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20](=[O:22])[CH3:21])=[CH:14][C:13]=2[F:23])[N:4]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:3]=1.[CH:34]1(B(O)O)[CH2:36][CH2:35]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH:34]1([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][C:9]=3[O:11][C:12]3[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20](=[O:22])[CH3:21])=[CH:14][C:13]=3[F:23])[N:4]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:3]=2)[CH2:36][CH2:35]1

参加物

9

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 59741006N-[4-({3-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide

生成物 1

HCID 59741001N-[4-({3-Cyclopropyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

1.00 g (1.86 mmol) of N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide, 1.12 g (13.1 mmol) of cyclopropylboronic acid (Wallace, Debra J.; Chen, Cheng-yi; Tetrahedron Lett. 2002, 43(39), 6987-6990), 52.3 mg (0.19 mmol) of tricyclohexylphosphine and 1.39 g (6.53 mmol) of potassium phosphate are suspended in 10 ml of toluene and 0.5 ml of water. The solution is degassed, and 20.9 mg (0.09 mmol) of palladium(II) acetate are added. The mixture is heated at 100° C. for 1.5 h. After cooling, ethyl acetate is added and the organic phase is separated off and washed twice with water. The organic phase is dried over sodium sulfate and concentrated. The product is purified by preparative HPLC.

後処理

  1. customThe solution is degassed
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. washwashed twice with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product is purified by preparative HPLC

出典と根拠

ORDレコード
ord-ef6747ea42574d43a07b33333ddc1c84
出典データセット
uspto-grants-2012_12
特許番号
US08329716B2

反応ノート

読み込み中…