Potassium Carbonate → HCID 11542926, compound

HRID 227920Notes

Reaction equation

HRID 227920 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[O:10]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11]1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+].O>[O:10]1[CH:14]=[CH:13][C:12]([C:2]2[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=2)=[CH:11]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 3491155-Bromothiophene-2-carboxylic acidHCID 2734358Furan-3-boronic acid

Product 1

HCID 11542926HCID 11542926, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonateCatalystHCID 962WaterSolvent

Procedure

Using microwave irradiation. The general procedure was used with 5-bromothiophene carboxylic acid (206 mg, 1.00 mmol), 3-furanboronic acid (168 mg, 1.50 mmol), Pd(OAc)2 (2.2 mg, 0.010 mmol, 1 mol %), sodium 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl-3′-sulfonate (10.0 mg, 0.020 mmol, 2 mol %), K2CO3 (414 mg, 3.00 mmol), water (5.0 mL), 10 min, 150° C. (using microwave irradiation with cooling). The product was isolated as a white solid (183 mg, 95%). Mp=147° C. 1H NMR (400 MHz, d4-MeOH) δ: 7.89 (m, 1H), 7.65 (d, 1H, J=4.0 Hz), 7.54 (t, 1H, J=1.6 Hz), 7.15 (d, 1H, J=4.0 Hz), 6.69 (m, 1H). 13C NMR (125 MHz, d4-MeOH) δ: 165.4, 145.6, 143.7, 140.9, 135.5, 132.9, 125.2, 121.5, 109.9. IR (neat, cm−1): 3200 (br), 1672, 1287. Anal. Calcd for C9H6O3S: C, 55.66; H, 3.11. Found: C, 55.50; H, 3.32.

Workup

  1. custommicrowave irradiation

Sources & evidence

ORD record
ord-4fec0234138e4f08bd9ff3ea5f276a60
Source dataset
uspto-grants-2009_07
Patent number
US07560596B2

Reaction notes

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