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

HRID 271054

반응식

HRID 271054 반응식
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

참가 물질

10

반응물 5

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

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6269621dd18f43c3b08ea6dfa06c56f1
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452876B2

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