Water → Tert-butyl[4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1h-imidazol-2-yl]-2-oxoethyl}phenyl)-1-methyl-1h-pyrazol-3-yl]carbamate

HRID 425364Notes

Reaction equation

HRID 425364 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[N:12]([S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])[CH:13]=[C:14]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[N:15]=2)=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:33][N:34]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[C:36]([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[N:35]1.O>CN(C)C=O.O>[C:51]([O:50][C:49](=[O:55])[NH:48][C:36]1[C:37]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]3[N:12]([S:21]([N:24]([CH3:26])[CH3:25])(=[O:22])=[O:23])[CH:13]=[C:14]([CH2:16][C:17]([CH3:18])([CH3:19])[CH3:20])[N:15]=3)=[O:10])=[CH:4][CH:3]=2)=[CH:38][N:34]([CH3:33])[N:35]=1)([CH3:54])([CH3:53])[CH3:52]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 591403972-[(4-bromophenyl)acetyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide2×HCID 77231560tert-butyl N-(1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-3-yl)carbamate

Product 1

HCID 131729424Tert-butyl[4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1h-imidazol-2-yl]-2-oxoethyl}phenyl)-1-methyl-1h-pyrazol-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (23 mg, 0.03 mmol) was added to a degassed, ambient temperature solution of 2-[(4-bromophenyl)acetyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (Intermediate 7) (123 mg, 0.28 mmol), sodium carbonate (89 mg, 0.84 mmol) and tert-butyl [1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-3-yl]carbamate (90 mg, 0.28 mmol) in N,N-dimethylformamide/water (2:1) (7.5 mL). After stirring at 80° C. overnight, the reaction mixture was cooled, poured into water and extracted with diethyl ether. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-30% acetone/methylene chloride afforded tert-butyl[4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1H-imidazol-2-yl]-2-oxoethyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate.

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cbcc07812cd4745a8f9364187bf5c63
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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