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

HRID 1525649ノート

反応式

HRID 1525649 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:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:22]=1[C:23]#[N:24].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl.O>[Cl:20][C:21]1[CH:28]=[C:27]([CH:26]=[CH:25][C:22]=1[C:23]#[N:24])[O:29][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

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 896195864-(Bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

生成物 1

HCID 716161464-[(3-chloro-4-cyanophenoxy)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 2-chloro-4-hydroxybenzonitrile (114 mg, 0.092 mmol) and K2CO3 (25 mg, 0.18 mmol). The reaction was stirred at room temperature for 16 hours. The reaction was diluted with DCM (10 mL) and water (20 mL). The organic layer was separated and the aqueous layer extracted with DCM (2×10 mL). The combined organic layers 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. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with DCM (2×10 mL)
  3. filtrationThe combined organic layers were filtered through a phase separation cartridge
  4. customto give a yellow oil which
  5. customwas purified by reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-5ea0b19e71e34514a5071bc35779f6c6
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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