Potassium Carbonate → HCID 86724052, compound

HRID 1753770Notes

Reaction equation

HRID 1753770 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:13][O:14][C:15]1[C:20](B(O)O)=[CH:19][CH:18]=[CH:17][N:16]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.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>[CH3:13][O:14][CH:15]1[C:20]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[O:12][CH:11]=[N:10][CH:9]=3)[CH:3]=2)=[CH:19][CH:18]=[CH:17][NH:16]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 27955655-(3-bromophenyl)-1,3-oxazole

Product 1

HCID 86724052HCID 86724052, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(3-bromo-phenyl)-oxazole VI-a (1.33 g, 5.94 mmol), 2-methoxy-3-pyridinylboronic acid (1.00 g, 6.53 mmol), Pd(PPh3)4 and K2CO3 (1.81 g, 13.1 mmol) in THF (20 mL) and water (10 mL) was heated to reflux for 4 h. The mixture was cooled, then diluted with water and extracted with EtOAc. The combined organics were dried (MgSO4), filtered and the residue purified by column chromatography (SiO2; eluting with 30% EtOAc in cyclohexane) to afford the desired product VI-b as brown oil which crystallized on standing (1.37 g, 91%). 1H NMR (300 MHz, CDCl3) δ 8.18 (dd, J=1.8, 5.0 Hz, 1H), 7.91 (s, 1H), 7.81 (s, 1H), 7.64 (d, J=6.9 Hz, 2H), 7.53-7.44 (m, 2H), 7.37 (s, 1H), 6.99 (dd, J=5.0, 7.2 Hz, 1H), 3.97 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. temperatureThe mixture was cooled
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. customthe residue purified by column chromatography (SiO2; eluting with 30% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-5afe80d53e164a4aab9c8d4e9e1ac992
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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