Potassium Carbonate → HCID 89633279、化合物

HRID 1525675ノート

反応式

HRID 1525675 の反応式
Br[CH2:2][C:3]1[C:15]([Cl:16])=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([F:17])[CH:4]=1.[Cl:18][C:19]1[CH:20]=[C:21]([OH:28])[CH:22]=[N:23][C:24]=1[CH:25]1[CH2:27][CH2:26]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:16][C:15]1[C:3]([CH2:2][O:28][C:21]2[CH:22]=[N:23][C:24]([CH:25]3[CH2:27][CH2:26]3)=[C:19]([Cl:18])[CH:20]=2)=[CH:4][C:5]([F:17])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 580424875-Chloro-6-cyclopropylpyridin-3-OLHCID 86702928HCID 86702928、化合物

生成物 1

HCID 89633279HCID 89633279、化合物収率 46%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a stirred solution of tert-butyl 4-(bromomethyl)-5-chloro-2-fluorobenzoate (Preparation 25, 2.50 g, 7.99 mmol) and 5-chloro-6-cyclopropylpyridin-3-ol (Preparation 42 WO2012007869, 1.13 g, 6.66 mmol) in DMSO (25 mL) was added K2CO3 (2.76 g, 19.9 mmol). The resulting mixture was stirred under nitrogen at room temperature for 18 hours. The reaction mixture was then quenched with water (30 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with water (30 mL), dried over MgSO4 and evaporated under reduced pressure to give the crude product (2.69 g). Purification was accomplished by column chromatography on silica (eluting with 1:9 Et2O/cyclohexane) affording the title compound (1.24 g, 46%).

後処理

  1. customThe reaction mixture was then quenched with water (30 mL)
  2. extractionextracted with EtOAc (2×30 mL)
  3. washThe combined organic layers were washed with water (30 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customto give the crude product (2.69 g)
  7. customPurification

出典と根拠

ORDレコード
ord-04f09de6b24243349d62b830e463d726
出典データセット
uspto-grants-2015_07
特許番号
US09085517B2

反応ノート

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