1,2-Dimethoxyethane → Ethyl 5-(2,5-difluorobenzyl)isoxazole-3-carboxylate

HRID 58571

반응식

HRID 58571 반응식
COCCOC.Br[CH2:8][C:9]1[O:13][N:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[CH2:8][C:9]1[O:13][N:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 13124955Ethyl 5-(bromomethyl)-1,2-oxazole-3-carboxylate

생성물 1

HCID 66831915Ethyl 5-(2,5-difluorobenzyl)isoxazole-3-carboxylate수율 59%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

1,2-Dimethoxyethane (8 mL) and water (2 mL) were added to the mixture of ethyl 5-(bromomethyl)isoxazole-3-carboxylate (1.00 g; 4.27 mmol), 2,5-difluorophenylboronic acid (0.773 g; 4.70 mmol), tetrakis(triphenylphosphine)palladium(0) (0.248 g; 0.640 mmol) and sodium carbonate (0.911 g; 8.55 mmol). The mixture was irradiated in a microwave oven at 130° C. for 20 minutes. After cooling, the reaction mixture was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (eluent: 5 to 40% of ethyl acetate in heptane) to give 0.67 g (59%) of ethyl 5-(2,5-difluorobenzyl)isoxazole-3-carboxylate as a yellow oil.

후처리

  1. customThe mixture was irradiated in a microwave oven at 130° C. for 20 minutes
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with ethyl acetate and water
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by flash chromatography on silica gel (eluent: 5 to 40% of ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-56c06f3f570d491c85ebf3b41cfd0baa
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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