Potassium Carbonate → HCID 11494967, compound

HRID 1991464Notes

Reaction equation

HRID 1991464 reaction equation
[CH2:1]([C:3]1[C:4]([CH3:21])=[C:5]2[C:12](I)=[C:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[S:10][C:6]2=[N:7][C:8]=1[CH3:9])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:3]1[C:4]([CH3:21])=[C:5]2[C:12]([C:33]3[CH:34]=[CH:35][C:30]([O:29][CH3:28])=[CH:31][CH:32]=3)=[C:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[S:10][C:6]2=[N:7][C:8]=1[CH3:9])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 59129741HCID 59129741, compound

Product 1

HCID 11494967HCID 11494967, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

To a solution of compound tert-butyl 5-ethyl-3-iodo-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylate (42 mg, 0.1 mmol) in 0.5 mL of DME/H2O (1/1) was added K2CO3 (41 mg, 0.3 mmol), Pd(PPh3)4 (12 mg, 0.01 mmol), p-methoxyphenyl boronic acid (18 mg, 0.12 mmol). The mixture was then heated to reflux for 16 h. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was dissolved with ethyl acetate (2 mL), washed with water (2 mL×3), brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude solid was purified by preparative HPLC to provide t-butyl 5-ethyl-3-(4-methoxy-phenyl)-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylate (12 mg, 30%).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 16 h
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved with ethyl acetate (2 mL)
  5. washwashed with water (2 mL×3), brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under reduced pressure
  8. customThe crude solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-5a8bc6aa07954f4587a2662268856e38
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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