Potassium Carbonate → 4-[(4-chloro-3-fluorophenoxy)methyl]-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

HRID 1525648ノート

反応式

HRID 1525648 の反応式
Br[CH2:2][C:3]1[C:17]([F:18])=[CH:16][C:6]([C:7]([NH:9][S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[O:8])=[C:5]([F:19])[CH:4]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[F:28].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl.O>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:2][C:3]2[C:17]([F:18])=[CH:16][C:6]([C:7]([NH:9][S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[O:8])=[C:5]([F:19])[CH:4]=2)=[CH:23][C:22]=1[F:28]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27245234-Chloro-3-fluorophenolHCID 896195864-(Bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

生成物 1

HCID 716161454-[(4-chloro-3-fluorophenoxy)methyl]-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-(bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide (Preparation 1, 33 mg, 0.092 mmol) in DMSO (1 mL) was added 4-chloro-3-fluorophenol (13.5 mg, 0.092 mmol) and K2CO3 (25 mg, 0.18 mmol). The reaction was stirred at room temperature for 3 hours and then at 40° C. for 16 hours. After 16 hours the reaction was diluted with DCM (10 mL) and water (20 mL). The organic was separated and the aqueous was extracted with DCM (2×10 mL). The combined organics were filtered through a phase separation cartridge and reduced to dryness to give a yellow oil which was purified by reverse phase preparative HPLC to afford the title compound.

後処理

  1. waitat 40° C. for 16 hours
  2. customThe organic was separated
  3. extractionthe aqueous was extracted with DCM (2×10 mL)
  4. filtrationThe combined organics were filtered through a phase separation cartridge
  5. customto give a yellow oil which
  6. customwas purified by reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-a16c593e7aab4a66b786d136bd89fc33
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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