Water → tert-butyl 9-isoxazol-4-yl-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 886927ノート

反応式

HRID 886927 の反応式
Br[C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[O:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1>[O:20]1[CH:24]=[C:23]([C:2]2[C:12]3[O:11][CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:22]=[N:21]1

参加物

6

反応物 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 164141804-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazoleHCID 59403519Tert-butyl 9-bromo-2,3-dihydrobenzo[F][1,4]oxazepine-4(5H)-carboxylate

生成物 1

HCID 68578732tert-butyl 9-isoxazol-4-yl-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate収率 62.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

A mixture of tert-butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (200 mg, 0.605 mmol), 4-isooxazolylboronic acid pinacol ester (119 mg, 0.609 mmol), tripotassium phosphate (194 mg, 0.914 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (24.9 mg, 0.0305 mmol) in dioxane (2 ml) was stirred at 85° C. for 12 hr under a nitrogen atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired product (120 mg, 62.2%) as an oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-08cfec8cf1284c1a92a64db3fd24c69b
出典データセット
uspto-grants-2012_08
特許番号
US08247403B2

反応ノート

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