Cesium carbonate → 6'-(3-(Cyclopropylamino)-6-methylbenzo[d]isoxazol-7-yl)spiro[cyclopentane-1,3'-indolin]-2'-one

HRID 2096989ノート

反応式

HRID 2096989 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[C:16]3[C:12]([C:13]4([CH2:22][CH2:21][CH2:20][CH2:19]4)[C:14](=[O:18])[NH:15]3)=[CH:11][CH:10]=2)O1.[CH:24]1([NH:27][C:28]2[C:32]3[CH:33]=[CH:34][C:35]([CH3:38])=[C:36](I)[C:31]=3[O:30][N:29]=2)[CH2:26][CH2:25]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH:24]1([NH:27][C:28]2[C:32]3[CH:33]=[CH:34][C:35]([CH3:38])=[C:36]([C:9]4[CH:17]=[C:16]5[C:12]([C:13]6([CH2:19][CH2:20][CH2:21][CH2:22]6)[C:14](=[O:18])[NH:15]5)=[CH:11][CH:10]=4)[C:31]=3[O:30][N:29]=2)[CH2:26][CH2:25]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 58702151N-cyclopropyl-7-iodo-6-methylbenzo[d]isoxazol-3-amineHCID 669537286'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,3'-indolin]-2'-one

生成物 1

HCID 444773826'-(3-(Cyclopropylamino)-6-methylbenzo[d]isoxazol-7-yl)spiro[cyclopentane-1,3'-indolin]-2'-one収率 28%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
105 °C

実験手順

An oven-dried resealable Schlenk tube was charged with 6′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,3′-indolin]-2′-one (preparation 4, 0.060 g, 0.19 mmol), N-cyclopropyl-7-iodo-6-methylbenzo[d]isoxazol-3-amine (WO2006094187, 0.090 g, 0.29 mmol), 1,4-dioxane (1.2 mL) and a 2M aqueous caesium carbonate solution (0.29 mL, 0.58 mmol). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.015 g, 0.02 mmol) was added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated in an oil bath to 100-110° C. After 20 hours, the mixture was cooled and partitioned between water and ethyl acetate. The organic extract was dried (MgSO4) and evaporated in vacuo. Purification of the residue by flash chromatography (98:2 dichloromethane/methanol) gave the title compound (0.017 g, 28%) as a yellow solid.

後処理

  1. additionwas added
  2. customAfter three further cycles of evacuation-backfilling with argon, the Schlenk tube was sealed
  3. temperaturethe mixture was cooled
  4. custompartitioned between water and ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated in vacuo
  8. customPurification of the residue by flash chromatography (98:2 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-9af6aa06bb5140f088b99066a7945096
出典データセット
uspto-grants-2013_05
特許番号
US08450341B2

反応ノート

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