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Triphenylphosphine → 6-(3-Phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

HRID 83252
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HRID 83252 반응식
[C:1]1([C:7]2[C:11]([CH2:12][OH:13])=[C:10]([C:14]([F:17])([F:16])[F:15])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24](O)=[N:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:18][O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([O:13][CH2:12][C:11]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][O:9][C:10]=2[C:14]([F:16])([F:17])[F:15])=[N:23][CH:22]=1
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6

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HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57732616(3-Phenyl-5-(trifluoromethyl)isoxazol-4-yl)methanolHCID 178498304HCID 178498304, 화합물

생성물 1

HCID 684432696-(3-Phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester수율 42.6%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

To a solution of (3-phenyl-5-trifluoromethyl-isoxazol-4-yl)-methanol (100 mg, 0.41 mmol) in THF (5 mL) was added 6-hydroxy-nicotinic acid methyl ester (69.3 mg, 0.45 mmol) and triphenylphosphine (162 mg, 0.62 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (96 μL, 0.62 mmol) was added and the reaction mixture was heated at 50° C. for 2 h. After cooling to room temperature the mixture was evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (66 mg, 42%) as all off-whit solid. MS: m/e=379.5 [M+H]+.

후처리

  1. temperatureAfter cooling to room temperature the mixture
  2. customwas evaporated
  3. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1)

출처 및 근거

ORD 기록
ord-8917978700054eb6a3e44d0dbc3262c9
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846719B2

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