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

HRID 2177712ノート

反応式

HRID 2177712 の反応式
[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

参加物

8

反応物 4

HCID 253881Sodium BromideHCID 23675105Potassium fluoride hydrateHCID 534270915-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-oxazoleHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
125 °C

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-025f47b8a83f4e668573a70bd0d335ba
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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