Sodium Carbonate → tert-Butyl(S)-1-(4-chlorophenyl)-4-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)-1H-pyrazol-1-yl)butan-2-ylcarbamate

HRID 598887

Reaction equation

HRID 598887 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8][C@@H:9]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:6]=1.CC1(C)C(C)(C)OB([C:34]2[CH:43]=[CH:42][C:37]3[NH:38][C:39](=[O:41])[O:40][C:36]=3[CH:35]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2C)CCCCC1>COCCOC.CCO.O.C([O-])(O)=O.[Na+].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]>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C@H:9]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:8][CH2:7][N:5]2[CH:6]=[C:2]([C:34]3[CH:43]=[CH:42][C:37]4[NH:38][C:39](=[O:41])[O:40][C:36]=4[CH:35]=3)[CH:3]=[N:4]2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27349382-(Dicyclohexylphosphino)-2'-methylbiphenylHCID 579506376-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2(3H)-oneHCID 57950651HCID 57950651, compound

Product 1

HCID 68373025tert-Butyl(S)-1-(4-chlorophenyl)-4-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)-1H-pyrazol-1-yl)butan-2-ylcarbamate

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 516892Sodium BicarbonateSolventHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (S)-tert-butyl 4-(4-bromo-1H-pyrazol-1-yl)-1-(4-chlorophenyl)butan-2-ylcarbamate (200 mg, 0.47 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2(3H)-one (183 mg, 0.70 mmol), sodium carbonate (148 mg, 1.40 mmol), 2-(dicyclohexylphosphino)-2′-methylbiphenyl (34.0 mg, 0.09 mmol), and bis(dibenzylideneacetone)palladium(0) (42.7 mg, 0.05 mmol) in DME:EtOH:H2O (7:2:3, 4 mL) was heated at 130° C. for 15 minutes in a Biotage Initiators microwave. After cooling to room temperature, the mixture was diluted with saturated aqueous NaHCO3 and extracted with DCM (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The material thus obtained was used without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with DCM (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material thus obtained
  7. customwas used without further purification

Sources & evidence

ORD record
ord-0c5b5cb5643b453bacc6f0195b49577b
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Linked notes

Loading…