Cesium carbonate → 3-(benzyloxy)-5-[4-chloro-3-(trifluoromethyl)phenyl]-1-(propan-2-yl)pyridin-2(1H)-one

HRID 625935Notes

Reaction equation

HRID 625935 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:19])[N:11]([CH:16]([CH3:18])[CH3:17])[CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=1[C:30]([F:33])([F:32])[F:31].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.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].C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10](=[O:19])[N:11]([CH:16]([CH3:18])[CH3:17])[CH:12]=[C:13]([C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:23]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27826714-Chloro-3-(trifluoromethyl)benzeneboronic acidHCID 674174683-(Benzyloxy)-5-bromo-1-(propan-2-yl)pyridin-2(1H)-one

Product 1

HCID 674185543-(benzyloxy)-5-[4-chloro-3-(trifluoromethyl)phenyl]-1-(propan-2-yl)pyridin-2(1H)-oneYield 113.3%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(Benzyloxy)-5-bromo-1-(propan-2-yl)pyridin-2(1H)-one (58 mg, 0.180 mmol), 4-chloro-3-(trifluoromethyl)phenylboronic acid (49 mg, 0.218 mmol), and Pd(dppf)Cl2—CH2Cl2 (8 mg, 9.80 μmol) were combined in THF (1 mL) in a microwave vessel. To this was added 1 M Cs2CO3 (0.540 mL, 0.540 mmol). The vessel was sealed then irradiated to 150° C. for 20 min. The layers were separated and the aqueous extracted with EtOAc (3×). The combined organic layers were filtered through a pad of silica gel washing with EtOAc. The filtrate was concentrated to give 3-(benzyloxy)-5-[4-chloro-3-(trifluoromethyl)phenyl]-1-(propan-2-yl)pyridin-2(1H)-one (86 mg) which was used directly in the next step without purification.

Workup

  1. customThe vessel was sealed
  2. customthen irradiated to 150° C. for 20 min
  3. customThe layers were separated
  4. extractionthe aqueous extracted with EtOAc (3×)
  5. filtrationThe combined organic layers were filtered through a pad of silica gel washing with EtOAc
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e22312228fc14570b594d56c93d78b25
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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