Methanol → 4-(Furan-2-yl)-1,3-thiazol-2-amine

HRID 737184Notes

Reaction equation

HRID 737184 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]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 4280242-Amino-4-bromothiazoleHCID 516892Sodium BicarbonateHCID 2734357Furan-2-boronic acid

Product 1

HCID 7278344-(Furan-2-yl)-1,3-thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customReaction mixture
  2. customwas degassed
  3. additionPd[P(Ph)3]4 (25 mg) was added
  4. customReaction mixture
  5. customwas brought to room temperature
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. custompurified

Sources & evidence

ORD record
ord-d72521ecc2654be1960ae04b50ff8c01
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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