Oxazole → HCID 67015701, compound

HRID 1618022Notes

Reaction equation

HRID 1618022 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[O:26]1[CH:30]=[CH:29][N:28]=[CH:27]1.CC(C)([O-])C.[Li+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:18][C:14]1[CH:13]=[C:12]([C:10](=[O:11])[CH2:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:27]3[O:26][CH:30]=[CH:29][N:28]=3)=[CH:3][CH:4]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 9255OxazoleHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 66666695(R)-3-(4-Bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

Product 1

HCID 67015701HCID 67015701, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

To a solution of (−)-3-(4-bromophenyl)-1-(2-methylpyridin-4-yl)-3-o-tolylpropan-1-one (120 mg; example 142, step 2), oxazole (126 mg) and tetrakis(triphenylphosphine) palladium(0) (68 mg) was added lithium tert-butoxide (141 mg) and the reaction mixture heated by microwave irradiation to 120° C. for 30 min. The reaction mixture was extracted over a sat. solution of sodium hydrogencarbonate (50 mL) with ethyl acetate (3×50 mL) and the combined organic phases dried over sodium sulfate. The crude reaction product was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane/ethyl acetate (1:1 to 2:1) to give the title compound as a colorless oil. MS (ESI+): m/z=383.0 ([M+H]+).

Workup

  1. extractionThe reaction mixture was extracted over a sat. solution of sodium hydrogencarbonate (50 mL) with ethyl acetate (3×50 mL)
  2. dry with materialthe combined organic phases dried over sodium sulfate
  3. customThe crude reaction product
  4. customwas purified by silica gel chromatography
  5. washeluting with a gradient of n-heptane/ethyl acetate (1:1 to 2:1)

Sources & evidence

ORD record
ord-26631bcb2611401c829c1b8c2ae5060d
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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