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

反応式

HRID 598887 の反応式
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

参加物

8

反応物 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、化合物

生成物 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

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 516892Sodium Bicarbonate溶媒HCID 86587095Dimethoxyethane ethanol water溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0c5b5cb5643b453bacc6f0195b49577b
出典データセット
uspto-grants-2011_03
特許番号
US07897619B2

関連ノート

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