Potassium Acetate → 2-(3-Ethylureido)-7-(pyridin-2-yl)benzothiazol-5-ylboronic acid
Reaction equation
[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]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
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%).
Workup
- customThe resulting reaction mixture
- customwas de-gassed
- customby purging N2 for 15-20 min
- customThe mixture was purged with N2 for 15-20 min
- additionThe reaction was poured onto saturated NH4Cl solution (1 L)
- filtrationThe resulting precipitate was filtered
- customdried under vacuum
- filtrationThe solution was filtered
- filtrationthe resulting solid collected by filtration
Sources & evidence
- ORD record
- ord-5a93c78a0be2407e9744a7851cffbfdb
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906902B2
Reaction notes
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