Sodium Bromide → Ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(oxazol-5-yl)benzoate

HRID 2177712노트

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HRID 2177712 반응식
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1(C)C(C)(C)OB([C:33]2[O:37][CH:36]=[N:35][CH:34]=2)O1.O.[F-].[K+].[Br-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([C:33]3[O:37][CH:36]=[N:35][CH:34]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

8

반응물 4

HCID 253881Sodium BromideHCID 23675105Potassium fluoride hydrateHCID 534270915-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-oxazoleHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2회

생성물 1

HCID 67107532Ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(oxazol-5-yl)benzoate수율 77.2%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
125 °C

실험 절차

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 0.1 g), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxazole (0.071 g), tetrakis-(triphenylphosphine) palladium (0.028 g), potassium fluoride monohydrate (0.102 g) and sodium bromide (0.045 g) in toluene (2 ml) was heated in a sealed tube under nitrogen at 125° C. for 18 hours. The mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(oxazol-5-yl)benzoate (0.075 g) as a yellow gum.

후처리

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

출처 및 근거

ORD 기록
ord-025f47b8a83f4e668573a70bd0d335ba
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

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