Potassium Acetate → 2-(3-Ethylureido)-7-(pyridin-2-yl)benzothiazol-5-ylboronic acid

HRID 1399965ノート

反応式

HRID 1399965 の反応式
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13](OS(C(F)(F)F)(=O)=O)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[B:30]1(B2OCC(C)(C)CO2)[O:35]CC(C)(C)C[O:31]1.CC([O-])=O.[K+]>CS(C)=O.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]>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([B:30]([OH:35])[OH:31])=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 517044Potassium AcetateHCID 2734316Bis(neopentyl glycolato)diboronHCID 72724619HCID 72724619、化合物

生成物 1

HCID 727244832-(3-Ethylureido)-7-(pyridin-2-yl)benzothiazol-5-ylboronic acid収率 88.6%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of xi (25 g, 56.1 mmol) in DMSO (250 mL) at RT was added bis(neopentylglycolato)diboron (25.2 g, 112 mmol) and KOAc (16.5 g, 168 mmol). The resulting reaction mixture was de-gassed by purging N2 for 15-20 min followed by addition of Pd(dppf)Cl2 (6.8 g, 8.4 mmol). The mixture was purged with N2 for 15-20 min and then heated to 80° C. for 90 min. The reaction was poured onto saturated NH4Cl solution (1 L). The resulting precipitate was filtered and dried under vacuum. The solid cake was taken in 2M NaOH (200 mL) and stirred for 45 min at RT. The solution was filtered and the filtrate was acidified up to pH 5-6 and the resulting solid collected by filtration to give Intermediate 1 (17 g, 88%).

後処理

  1. customThe resulting reaction mixture
  2. customwas de-gassed
  3. customby purging N2 for 15-20 min
  4. customThe mixture was purged with N2 for 15-20 min
  5. additionThe reaction was poured onto saturated NH4Cl solution (1 L)
  6. filtrationThe resulting precipitate was filtered
  7. customdried under vacuum
  8. filtrationThe solution was filtered
  9. filtrationthe resulting solid collected by filtration

出典と根拠

ORDレコード
ord-5a93c78a0be2407e9744a7851cffbfdb
出典データセット
uspto-grants-2014_12
特許番号
US08906902B2

反応ノート

読み込み中…