Sodium Carbonate → HCID 21084269, compound

HRID 348278Notes

Reaction equation

HRID 348278 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.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>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=3)[CH:3]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 22261247HCID 22261247, compound

Product 1

HCID 21084269HCID 21084269, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
85 °C

Procedure

2-[2-(3-Bromo-phenyl)-5-methyloxazol-4-yl]ethanol (1.0 g, 3.54 mmol) (see Ex. 2, Part D) and para-fluorophenyl boronic acid (744 mg, 5.32 mmol) were stirred in n-PrOH (10 mL) under nitrogen, to which 2M Na2CO3 (3.54 mL) was added. The mixture was heated at 85° C., and after Pd(PPh3)4 (41 mg, 0.0354 mmol) was added, the reaction proceeded for 0.5 h. Once the reaction mixture had cooled to room temperature, it was concentrated and taken up in CH2Cl2 (20 mL), then washed with 0.5M NaOH (20 mL). The aqueous layer was back-extracted with CH2Cl2 (10 mL), combined organics were washed with 1M NaOH (10 mL), followed by H2O (10 mL), then dried over Na2SO4, and concentrated to a crude solid. Recrystallized from ethyl acetate:hexanes (1:1) and vacuum oven-dried at 50° C. to yield a tan solid (375 mg, 36%). 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 7.96 (d, J=7.6 Hz, 1H) 7.63–7.59 (m, 3H), 7.50 (t, J=7.6 Hz, 1H), 7.18–7.13 (m, 2H) 3.95 (t, J=5.6 Hz, 2H), 2.76 (t, J=5.6 Hz, 2H), 2.37 (s, 3H); MS (EI) 298.1 (M+H)+.

Workup

  1. additionwas added
  2. temperatureOnce the reaction mixture had cooled to room temperature
  3. concentrationit was concentrated
  4. washwashed with 0.5M NaOH (20 mL)
  5. extractionThe aqueous layer was back-extracted with CH2Cl2 (10 mL)
  6. washcombined organics were washed with 1M NaOH (10 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to a crude solid
  9. customRecrystallized from ethyl acetate:hexanes (1:1) and vacuum
  10. customoven-dried at 50° C.

Sources & evidence

ORD record
ord-1b8a809f27154f60aa20ea6e9402463d
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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