Potassium Carbonate → HCID 25182139, compound

HRID 2193454Notes

Reaction equation

HRID 2193454 reaction equation
[CH2:1]([C:4]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH2:1]([C:4]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:12]=[C:13]([C:28]3[CH:27]=[CH:26][C:25]([F:24])=[CH:30][C:29]=3[F:31])[CH:14]=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 25182140HCID 25182140, compound

Product 1

HCID 25182139HCID 25182139, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-allyl-3-(3-bromophenyl)-6-phenyl-1,3-oxazinan-2-one (50 mg, 0.134 mmol) and 2,4-difluorophenylboronic acid (40 mg, 0.215 mmol), K2CO3 (0.5 mL, 2 M) in 1,4-dioxane (1.5 ml) was slowly added Pd(Ph3)2Cl2 (10 mg, 20%) at 0° C. under N2. The mixture was refluxed overnight. The mixture was concentrated to give the crude product, which was purified by TLC and preparative HPLC to afford 6-allyl-3-(2′,4′-difluorobiphenyl-3-yl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 18%). 1H NMR (400 MHz, CDCl3): δ=2.40 (m, 2H), 2.55-2.72 (m, 2H), 3.26 (m, 1H), 3.47 (m, 1H), 5.05 (m, 2H), 5.76 (m, 1H), 6.76-6.90 (m, 2H), 7.04 (m, 1H), 7.28 (m, 4H), 7.36 (m, 2H).

Workup

  1. customat 0° C.
  2. temperatureThe mixture was refluxed overnight
  3. concentrationThe mixture was concentrated
  4. customto give the crude product, which
  5. customwas purified by TLC and preparative HPLC

Sources & evidence

ORD record
ord-40901d10e2184fceb49b7105afd8a3e4
Source dataset
uspto-grants-2012_12
Patent number
US08329897B2

Reaction notes

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