Methyl 2,4-Difluorobenzoate → Methyl 2-(6-(benzyloxy)pyridin-3-yloxy)-4-fluorobenzoate

HRID 573106노트

반응식

HRID 573106 반응식
[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].F[C:23]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26]>CC1CCCO1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]([O:15][C:23]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:24]=2[C:25]([O:27][CH3:28])=[O:26])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 2782897Methyl 2,4-DifluorobenzoateHCID 23665647Potassium tert-butoxideHCID 425530416-(Benzyloxy)pyridin-3-ol

생성물 1

HCID 67228431Methyl 2-(6-(benzyloxy)pyridin-3-yloxy)-4-fluorobenzoate

시약·촉매·용매 2

HCID 73012-Methyltetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
75 °C

실험 절차

To 6-(benzyloxy)pyridin-3-ol (1.10 g) in 2-methyltetrahydrofuran (20 mL) was added potassium t-butoxide (5.47 mL, 1.0M in tetrahydrofuran). After stirring for 15 minutes, methyl 2,4-difluorobenzoate (1.035 g) in 2-methyltetrahydrofuran (2 mL) was added and the reaction heated to 75° C. for 1 hour. The reaction was cooled, diluted with ethyl acetate (150 mL), washed with water (50 mL), brine (50 mL), dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (SF40-80 g) eluting with a gradient of 5% to 20% ethyl acetate/hexanes gave the title compound.

후처리

  1. temperatureThe reaction was cooled
  2. washwashed with water (50 mL), brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washSilica gel chromatography (SF40-80 g) eluting with a gradient of 5% to 20% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-81af208bf7a94fb2b2b9fb56bc926999
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029404B2

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