2-(Dimethylamino)ethanol → (E)-N-(3-(2-ethoxyvinyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide

HRID 1256093ノート

反応式

HRID 1256093 の反応式
Br[C:2]1[CH:3]=[C:4]([NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH:5]=[CH:6][C:7]=1[S:8](=[O:21])(=[O:20])[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:17][O:16][B:15]([OH:18])[C:14]=2[CH:19]=1.C([Sn](CCCC)(CCCC)/[CH:34]=[CH:35]/[O:36][CH2:37][CH3:38])CCC.CN(CCO)C>CN1C(=O)CCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:37]([O:36]/[CH:35]=[CH:34]/[C:2]1[CH:3]=[C:4]([NH:22][C:23](=[O:28])[C:24]([F:26])([F:27])[F:25])[CH:5]=[CH:6][C:7]=1[S:8](=[O:20])(=[O:21])[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:17][O:16][B:15]([OH:18])[C:14]=2[CH:19]=1)[CH3:38]

参加物

6

反応物 3

HCID 79022-(Dimethylamino)ethanolHCID 6508882Stannane, tributyl(2-ethoxyethenyl)-HCID 86655204N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide

生成物 1

HCID 86655212(E)-N-(3-(2-ethoxyvinyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

The mix of N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide (87 mg, 0.182 mmol), (E)-tributyl(2-ethoxyvinyl) stannane (71 mg, 0.196 mmol), dimethylamino ethanol (17.9 mg, 0.2 mmol) and Pd(dppf)2Cl2 in NMP (2 ml) was degassed and heated to 100° C. overnight. The crude product was purified by prep-HPLC to give (E)-N-(3-(2-ethoxyvinyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide.

後処理

  1. customwas degassed
  2. customThe crude product was purified by prep-HPLC

出典と根拠

ORDレコード
ord-e9b0dc2119444dc39faf782e8ca09162
出典データセット
uspto-grants-2013_06
特許番号
US08461134B2

反応ノート

読み込み中…