8-Hydroxyquinoline → 4-hydroxymethyl-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)imidazole

HRID 559534ノート

反応式

HRID 559534 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[CH:4][C:3]=1[F:15].[OH:16][CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[OH:16][CH2:17][C:18]1[N:19]=[C:20]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]3=[O:14])=[CH:4][C:3]=2[F:15])[NH:21][CH:22]=1

参加物

6

反応物 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 593866611-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzeneHCID 178519868HCID 178519868、化合物

生成物 1

HCID 1785160734-hydroxymethyl-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)imidazole

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Alternatively as shown in Scheme 4, 1-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzene 3-2 prepared as above, is treated with 4-hydroxymethylimidazole II-1 in the presence of 8-hydroxyquinoline, and K2CO3 in DMSO. The resulting mixture is degassed before being charged with CuI to give 4-hydroxymethyl-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)imidazole 4-1. The compound 4-1 is treated with thionyl chloride to give 4-chloromethyl-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)imidazole which is then treated with NaN3 to result in 4-azidomethyl-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)imidazole 4-2. The azide 4-2 is reduced with Ph3P to give 4-aminomethyl-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)imidazole 4-3. The compound 4-3 is then treated with 5-chlorothiophene-2-carboxylic acid 1-5 to give the title compound 21.

後処理

  1. customprepared as above,
  2. customThe resulting mixture is degassed
  3. additionbefore being charged with CuI

出典と根拠

ORDレコード
ord-27173d73080c426c8215d33be38ff609
出典データセット
uspto-grants-2011_11
特許番号
US08063077B2

反応ノート

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