Triphenylphosphine → 5-Bromo-2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine

HRID 83114

반응식

HRID 83114 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].O[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][N:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:17][CH:18]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 178515818HCID 178515818, 화합물

생성물 1

HCID 684448075-Bromo-2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine수율 42%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (189 mg, 1.0 mmol) in THF (12 mL) was added 2-hydroxy-5-bromopyridine (191 mg, 1.1 mmol) and triphenylphosphine (393 mg, 1.5 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (233 μL, 1.5 mmol) was added and the reaction mixture was stirred for 3 h at room temperature. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (144 mg, 42%) as a colourless gum. MS: m/e=345.0/347.1 [M+H]+.

후처리

  1. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1)

출처 및 근거

ORD 기록
ord-1c7839e916734be68ac34b58a076b900
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846719B2

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