Methanol → 4-(Furan-2-yl)-1,3-thiazol-2-amine
Reaction equation
Br[C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O.CO.C([O-])(O)=O.[Na+]>CN(C=O)C>[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
4-Bromo-thiazol-2-ylamine (100 mg, 0.34 mmol) was combined with 57 mg (0.51 mmol) of 2-furan boronic acid. To this mixture was added 5 mL of MeOH, 1 mL of sat. NaHCO3 (aq), and 0.8 mL of DMF. Reaction mixture was degassed and Pd[P(Ph)3]4 (25 mg) was added. Reaction mixture was heated at 70° C. for 7 hours. The reaction mixture was brought to room temperature and filtered. The filtrate was evaporated and purified using reverse phase HPLC.
Workup
- customReaction mixture
- customwas degassed
- additionPd[P(Ph)3]4 (25 mg) was added
- customReaction mixture
- customwas brought to room temperature
- filtrationfiltered
- customThe filtrate was evaporated
- custompurified
Sources & evidence
- ORD record
- ord-d72521ecc2654be1960ae04b50ff8c01
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595398B2
Reaction notes
Loading…