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

반응식

HRID 598887 반응식
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

참가 물질

8

반응물 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, 화합물

생성물 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

시약·촉매·용매 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 516892Sodium Bicarbonate용매HCID 86587095Dimethoxyethane ethanol water용매

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온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0c5b5cb5643b453bacc6f0195b49577b
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897619B2

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