Dichloromethane → 3-(benzyloxy)-5-(biphenyl-3-yl)-1-methylpyridin-2(1H)-one

HRID 625940Notes

Reaction equation

HRID 625940 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1COCC1>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13]([C:29]2[CH:28]=[C:27]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:32]=[CH:31][CH:30]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2734315(3-Phenylphenyl)boronic acidHCID 674178603-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one

Product 1

HCID 674189793-(benzyloxy)-5-(biphenyl-3-yl)-1-methylpyridin-2(1H)-oneYield 72%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 3-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one (38 mg, 0.129 mmol), biphenyl-3-ylboronic acid (31 mg, 0.155 mmol), PdCl2(dppf).CH2Cl2 (5.3 mg, 0.006 mmol), under nitrogen, was added THF (1 mL) followed by 1 M aqueous Na2CO3 solution (0.388 mL). The reaction mixture was heated at 150° C. (microwave irradiation) for 25 min, cooled to room temperature and partitioned between water and EtOAc. Layers were separated and the aqueous solution was extracted with CH2Cl2 (2×). Combined organic solutions were dried over Na2SO4 and concentrated. Purification by flash chromatography (24 g silica gel, 3% to 100% EtOAc in hexanes) afforded 34 mg (72%) of 3-(benzyloxy)-5-(biphenyl-3-yl)-1-methylpyridin-2(1H)-one as a white solid. LC/MS (M+H)+ 368.3.

Workup

  1. custom(microwave irradiation) for 25 min
  2. temperaturecooled to room temperature
  3. custompartitioned between water and EtOAc
  4. customLayers were separated
  5. extractionthe aqueous solution was extracted with CH2Cl2 (2×)
  6. dry with materialCombined organic solutions were dried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by flash chromatography (24 g silica gel, 3% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7fcf369503fe4290911d629d2502ae8d
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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