Potassium Phosphate, Tribasic → N-(4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)ethanesulfonamide

HRID 632746ノート

反応式

HRID 632746 の反応式
[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[C:5]2[CH:17]=[CH:18][N:19]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:4]=2[C:3]1=[O:30].Br[C:32]1[CH:33]=[C:34]([NH:47][S:48]([CH2:51][CH3:52])(=[O:50])=[O:49])[CH:35]=[CH:36][C:37]=1[O:38][C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=1[F:46].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].CC12CC3(C)P(C4C=CC=CC=4)C(C)(CC(C)(O3)O1)O2>[F:46][C:40]1[CH:41]=[C:42]([F:45])[CH:43]=[CH:44][C:39]=1[O:38][C:37]1[CH:32]=[CH:33][C:34]([NH:47][S:48]([CH2:51][CH3:52])(=[O:49])=[O:50])=[CH:35][C:36]=1[C:6]1[C:5]2[CH:17]=[CH:18][N:19]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:4]=2[C:3](=[O:30])[N:2]([CH3:1])[CH:7]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 867210626-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-oneHCID 117770988N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamide

生成物 1

HCID 117773894N-(4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)ethanesulfonamide収率 93.1%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 534277901,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane触媒

反応条件

温度
60 °C

実験手順

A mixture of 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (6.00 g, 14.0 mmol), N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamide (5.77 g, 14.7 mmol), 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (0.205 g, 0.700 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.321 g, 0.350 mmol) and potassium phosphate (2.97 g, 14.0 mmol) was combined and sparged with argon for 30 minutes. A mixture of dioxane (60 mL) and water (15 mL) was sparged with nitrogen for 30 minutes and transferred by syringe into the reaction vessel under argon. The reaction mixture was stirred at 60° C. for 2 hours, cooled to ambient temperature, and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (anhydrous sodium sulfate), treated with silica gel (2-4 g) for 45 minutes, filtered and concentrated to afford N-(4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)ethanesulfonamide (8 g, 13.04 mmol, 93% yield).

後処理

  1. customsparged with argon for 30 minutes
  2. additionA mixture of dioxane (60 mL) and water (15 mL)
  3. customwas sparged with nitrogen for 30 minutes
  4. customtransferred by syringe into the reaction vessel under argon
  5. temperaturecooled to ambient temperature
  6. custompartitioned between ethyl acetate and water
  7. washThe organic layer was washed with brine
  8. dry with materialdried (anhydrous sodium sulfate)
  9. additiontreated with silica gel (2-4 g) for 45 minutes
  10. filtrationfiltered
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-99fabf65b0754003af0efabd2db932f5
出典データセット
uspto-grants-2016_04
特許番号
US09321765B2

反応ノート

読み込み中…