Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)- → 5-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36289

反応式

HRID 36289 の反応式
Br[C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH3:15])=[N:10][N:9]([C:16]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=3[Cl:25])[C:8]2=[O:26])=[C:4]([F:29])[CH:3]=1.[C:30]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1B(O)O)(=[O:37])=[O:36])([CH3:33])([CH3:32])[CH3:31]>[Pd]>[CH2:12]([C:11]1[N:7]([CH2:6][C:5]2[CH:27]=[CH:28][C:2]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[S:35](=[O:37])(=[O:36])[NH:34][C:30]([CH3:31])([CH3:33])[CH3:32])=[CH:3][C:4]=2[F:29])[C:8](=[O:26])[N:9]([C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=2[Cl:25])[N:10]=1)[CH2:13][CH2:14][CH3:15]

参加物

4

反応物 2

HCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-HCID 199394724-(4-Bromo-2-fluorobenzyl)-5-n-butyl-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

生成物 1

HCID 104614745-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one収率 52%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

The palladium(0)-catalyzed coupling of 4-(4-bromo-2-fluorobenzyl)-5-n-butyl-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step A) with 2-(N-t-butylsulfamoyl)phenylboronic acid was carried out according to the procedure of Example 76, Step F. Purification of the crude product by flash chromatography on silica gel (gradient elution with 6:1 to 4:1 hexane-EtOAc) provided a 52% yield of the title compound as a pale yellow, stiff foam, mp 124°-126° C.; homogeneous by TLC in 4:1 hexane-EtOAc); mass spectrum (FAB) m/e 616 (M+1)+.

後処理

  1. customPurification of the crude product by flash chromatography on silica gel (gradient elution with 6:1 to 4:1 hexane-EtOAc)

出典と根拠

ORDレコード
ord-b72ffebebf9e4f8ea34f6cc0fb559014
出典データセット
uspto-grants-1995_05
特許番号
US05411980

関連ノート

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