Sodium Carbonate → HCID 69871063, compound

HRID 398134Notes

Reaction equation

HRID 398134 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[C:5]([CH3:38])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26](B4OC(C)(C)C(C)(C)O4)=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[CH3:6])[CH3:2].Br[C:41]1[CH:42]=[N:43][CH:44]=[N:45][CH:46]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(C)C>[CH2:1]([O:3][C:4](=[O:39])[C:5]([CH3:38])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:24]=[CH:25][C:26]([C:41]4[CH:42]=[N:43][CH:44]=[N:45][CH:46]=4)=[CH:27][CH:28]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[CH3:6])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 783445-BromopyrimidineHCID 23589997HCID 23589997, compound

Product 1

HCID 69871063HCID 69871063, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
86 °C

Procedure

A 50 mL flask was charged with 2-methyl-2-[4-(2-{5-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazol-4-yl}-ethoxy)-phenoxy]-propionic acid ethyl ester (198 mg, 0.371 mmol), 5-bromopyrimidine (54 mg, 338 mmol), and 5 mL of isopropanol. The flask was purged with N2 three times. After 20 min, palladium acetate (3.0 mg, 0.04 mmol) and triphenylphosphine (3.5 mg, 0.04 mmol) were added. Following addition of a solution of sodium carbonate (43 mg in 1 mL H2O), the mixture was heated to 86° C. for 4 h. The solvent was removed under reduced pressure and the remaining residue taken up in CH2Cl2 (25 mL) and extracted with 0.5 N NaOH (25 mL). The aqueous layer was back extracted with an additional 25 mL CH2Cl2 and the organic layers combined. The organic layer was washed with 1 N NaOH (25 mL) and H2O (25 mL) and then dried and concentrated in vacuo. Flash chromatography provided the desired product. 1H NMR (400 MHz, CDCl3) δ9.23 (s, 1 H), 9.20 (s, 2 H), 8.16 (d, 2 H), 7.65 (d, 2 H), 6.88 (d, 2 H), 6.75 (d, 2 H), 4.21 (q, 2 H), 4.20 (t, 2 H), 3.00 (t, 2 H), 2.39 (s, 3 H), 1.48 (s, 6 H), 1.21 (t, 3 H); MS (EI) 488.1 (M+H)+.

Workup

  1. customThe flask was purged with N2 three times
  2. customThe solvent was removed under reduced pressure
  3. extractionextracted with 0.5 N NaOH (25 mL)
  4. extractionThe aqueous layer was back extracted with an additional 25 mL CH2Cl2
  5. washThe organic layer was washed with 1 N NaOH (25 mL) and H2O (25 mL)
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d77026d5e5f84a8c9144524e3bec29f9
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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