1,2-Dimethoxyethane → Ethyl 2-(2-aminopyridin-4-yl)oxazole-4-carboxylate

HRID 632817노트

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HRID 632817 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)O1.Br[C:18]1[O:19][CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:22]=1.C(=O)([O-])[O-].[K+].[K+].COCCOC>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[NH2:15][C:11]1[CH:10]=[C:9]([C:18]2[O:19][CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:22]=2)[CH:14]=[CH:13][N:12]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 26370035Ethyl 2-bromo-1,3-oxazole-4-carboxylateHCID 457857074-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

생성물 1

HCID 118061442Ethyl 2-(2-aminopyridin-4-yl)oxazole-4-carboxylate수율 31.3%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회

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온도
80 °C

실험 절차

To a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (4.28 g), ethyl 2-bromo-1,3-oxazole-4-carboxylate (4.28 g), potassium carbonate (5.38 g) and DME (78 mL)/water (19.45 mL) was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (0.712 g), and the mixture was stirred at 80° C. for 3 hr under argon atmosphere, poured into water, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (1.42 g).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-a20cc8f028364bad9735275edc113a10
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321757B2

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