Phenylboronic Acid → HCID 25183175, compound

HRID 450976Notes

Reaction equation

HRID 450976 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][C:11]([CH3:20])([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:10][C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])(O)=O.[Na+]>C1COCC1.O>[C:2]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:13][CH2:12][C:11]([CH3:20])([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:10][C:9]2=[O:21])[CH:3]=1

Participants

6

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 25183312HCID 25183312, compound

Product 1

HCID 25183175HCID 25183175, compoundYield 20.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-bromophenyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (50 mg, 0.14 mmol) and phenylboronic acid (35 mg, 0.29 mmol) in THF (2 mL) was added a solution of NaHCO3 (31 mg, 0.29 mmol) in H2O (2 mL) followed by Pd(PPh3)Cl2 (9 mg, 0.01 mmol). The mixture was refluxed overnight. The mixture was concentrated to give the crude product, which was purified by column chromatography, followed by preparative HPLC to afford 3-(biphenyl-3-yl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (10 mg, 20%). 1H NMR: (400 MHz, CDCl3): δ 1.71 (s, 3H), 2.40 (m, 1H), 2.48 (m, 1H), 3.31 (m, 1H), 3.54 (m, 1H), 7.08 (m, 1H), 7.30 (m, 3H), 7.7.32-7.42 (m, 8H), 7.46 (m, 2H). LC-MS Method 3, tR=1.362 min, m/z=344. 1H NMR (CDCl3) 1.75 (s, 3H), 2.32-2.43 (m, 1H), 2.50 (m, 1H), 3.20 (m, 1H), 3.52 (m, 1H), 7.10 (d, 1H), 7.25-7.45 (m, 11H), 7.50 (d, 2H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationThe mixture was concentrated
  3. customto give the crude product, which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1317584169ac4fb681e616d5bbb25383
Source dataset
uspto-grants-2013_07
Patent number
US08487094B2

Reaction notes

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