Cesium carbonate → HCID 58109531, compound

HRID 2037445Notes

Reaction equation

HRID 2037445 reaction equation
[CH2:1]([C:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([CH:11]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][N:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[F:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([C:31]3[CH:30]=[CH:29][C:28]([F:27])=[CH:33][C:32]=3[F:34])=[CH:15][N:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343342,4-Difluorophenylboronic acidHCID 58109227HCID 58109227, compound

Product 1

HCID 58109531HCID 58109531, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-allyl-3-(1-(5-bromopyridin-2-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (100 mg, 0.24 mmol), 2,4-difluorophenylboronic acid (56.9 mg, 0.36 mmol), PdCl2(PPh3)2 (10 mg, 10%) and aqueous solution of Cs2CO3 (2 M, 0.2 mL) in 1,4-dioxane (3 mL) was heated to reflux overnight. After the solvents were evaporated, the crude product was purified by preparative TLC to give 6-allyl-3-(1-(5-(2,4-difluorophenyl)pyridin-2-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (50 mg, 46%). LC-MS Method 3, tR=1.336 min, m/z=453.1. 1H NMR (CDCl3): 2.30-2.40 (m, 1H), 2.39-2.42 (d, 3H), 2.50-2.60 (m, 2H), 2.60-2.70 (m, 2H), 4.10-4.20 (m, 1H), 4.50-4.65 (m, 2H), 5.55-5.70 (m, 2H), 6.40-6.50 (d, 1H), 6.80-7.00 (m, 4H), 7.10-7.15 (m, 1H), 7.22-7.30 (m, 2H), 7.30-7.40 (m, 3H).

Workup

  1. temperatureto reflux overnight
  2. customAfter the solvents were evaporated
  3. customthe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-bf1112874b6b4d1c801e408adc402094
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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