Formic Acid → 4-Amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylic acid

HRID 573548Notes

Reaction equation

HRID 573548 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([Br:25])=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[C:3]=12.[OH-].[Na+].C(O)=O>CS(C)=O.O>[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([Br:25])=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[C:3]=12

Participants

6

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 68324129Ethyl 4-amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate

Product 1

HCID 683238684-Amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylic acidYield 78.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 4-amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate (700 mg, 1.661 mmol) (Description 15) in DMSO (7 mL) and aqueous NaOH (2M) (4.15 mL, 8.31 mmol) was heated at 150° C. for 1 h. The mixture was cooled to RT, diluted with water (20 mL) and acidified with formic acid to pH 6. The mixture was then extracted with ethyl acetate (5×30 mL) and the combined organics washed with brine (2×30 mL), dried and concentrated, to give the title compound (513 mg). LCMS (A) m/z: 393/395 [M+1]+, Rt 1.04 min (acidic).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionThe mixture was then extracted with ethyl acetate (5×30 mL)
  3. washthe combined organics washed with brine (2×30 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-03fc299270764811957c29dd2eeb2f6d
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

Loading…