Hydrochloric Acid → 3-cyclohexyl-N-(N,N-dimethylsulfamoyl)-2-(2-formyl-4-methoxyphenyl)-1H-indole-6-carboxamide

HRID 747941

反応式

HRID 747941 の反応式
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([NH:19][S:20]([N:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])=[O:18])[CH:5]=2.B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2[C:42]2[C:47]([O:48][CH3:49])=[CH:46][CH:45]=[CH:44][C:43]=2OC)CCCCC1.[C:58](=O)([O-])[O-:59].[K+].[K+].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([NH:19][S:20](=[O:22])(=[O:21])[N:23]([CH3:25])[CH3:24])=[O:18])=[CH:7][CH:8]=3)[NH:3][C:2]=2[C:44]2[CH:45]=[CH:46][C:47]([O:48][CH3:49])=[CH:42][C:43]=2[CH:58]=[O:59])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 61668Boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 587651502-bromo-3-cyclohexyl-N-(dimethylsulfamoyl)-1H-indole-6-carboxamide

生成物 1

HCID 597500763-cyclohexyl-N-(N,N-dimethylsulfamoyl)-2-(2-formyl-4-methoxyphenyl)-1H-indole-6-carboxamide

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2 回

実験手順

A mixture of the 2-Bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-1H-indole-6-carboxamide (4.28 g, 0.01 mol), boronic acid (2.7 g, 0.015 mol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-biphenyl (41 mg, 0.0001 mol), palladium acetate (11.2 mg), and finely ground potassium carbonate (4.24 g, 0.02 mol) in toluene (30 mL) was stirred under reflux and under nitrogen for 30 min, at which time LC/MS analysis showed the reaction to be complete. The reaction mixture was then diluted with ethyl acetate and water, and then acidified with an excess of dilute HCl. The ethyl acetate layer was then collected and washed with dilute HCl, water and brine. The organic solution was then dried (magnesium sulfate), filtered and concentrated to give a gum. The gum was diluted with hexanes (250 ml) and ethyl acetate (25 mL), and the mixture was stirred for 20 hr at 22° C. during which time the product was transformed into a bright yellow granular solid (4.8 g) which was used directly without further purification.

後処理

  1. temperatureunder reflux and under nitrogen for 30 min, at which time LC/MS analysis
  2. customthe reaction
  3. customThe ethyl acetate layer was then collected
  4. washwashed with dilute HCl, water and brine
  5. dry with materialThe organic solution was then dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a gum
  9. stirringthe mixture was stirred for 20 hr at 22° C. during which time the product
  10. customwas used directly without further purification

出典と根拠

ORDレコード
ord-4955b3604e914effbeaea25cebc964e3
出典データセット
uspto-grants-2008_07
特許番号
US07399758B2

関連ノート

読み込み中…