Potassium Carbonate → HCID 86656574, compound

HRID 243570Notes

Reaction equation

HRID 243570 reaction equation
Cl[C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][S:10][C:5]2=[CH:4][C:3]=1[CH:11]=[O:12].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>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>[C:13]1([C:2]2[N:7]=[C:6]3[CH:8]=[CH:9][S:10][C:5]3=[CH:4][C:3]=2[CH:11]=[O:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 124155695-Chlorothieno[3,2-b]pyridine-6-carboxaldehyde

Product 1

HCID 86656574HCID 86656574, compoundYield 86.5%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To a solution of 5-chlorothieno[3,2-b]pyridine-6-carbaldehyde (396 mg, 2.01 mmol) in DME/water (10 mL/2 mL) was added phenylboronic acid (306 mg, 2.51 mmol), K2CO3 (833 mg, 6.03 mmol) and Pd(PPh3)4 (116 mg, 0.1 mmol). The mixture was degassed before being heated in a sealed tube at 100° C. for 5 h. The reaction mixture was allowed to cool to room temperature, diluted with EtOAc (25 mL), washed with water (2×10 mL) and washed with brine (10 mL). The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by column chromatography (SiO2, 0-40% EtOAc in heptane) to give the title compound (416 mg, 86%) as a white solid. δH (CDCl3) 10.15 (s, 1H), 8.88 (s, 1H), 8.97 (d, J 6 Hz, 1H), 7.69 (d, J 6 Hz, 1H), 7.50-7.65 (m, 5H). LCMS (ES+) 240.2 (M+H)+, RT 3.46 minutes (Method 2).

Workup

  1. customThe mixture was degassed
  2. temperatureto cool to room temperature
  3. additiondiluted with EtOAc (25 mL)
  4. washwashed with water (2×10 mL)
  5. washwashed with brine (10 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customThe residue was purified by column chromatography (SiO2, 0-40% EtOAc in heptane)

Sources & evidence

ORD record
ord-77e5368df97b4007a1cf553f03dbebf5
Source dataset
uspto-grants-2014_02
Patent number
US08653272B2

Reaction notes

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