Ethyl Acetate → HCID 67536812, compound

HRID 1496630Notes

Reaction equation

HRID 1496630 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[N:8]=1)([CH3:3])[CH3:2].Br[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=1.C([O-])(=O)C.[K+].C(OCC)(=O)C>CC(N(C)C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[N:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[S:5][C:6]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 517044Potassium AcetateHCID 27628354-Bromo-2-methylpyridineHCID 67435246HCID 67435246, compound

Product 1

HCID 67536812HCID 67536812, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

Under argon, 200 mg (0.90 mmol) of 2-isopropyl-4-(4-fluorophenyl)-1,3-thiazole, 77 mg (0.45 mmol) of 4-bromo-2-methylpyridine, 133 mg (1.35 mmol) of potassium acetate and 0.4 mg (2 μmol) of palladium(II) acetate in 5 ml of DMA are heated to 150° C. After 3 h, 50 ml of ethyl acetate are added and the reaction mixture is filtered through a silica gel cartridge. 10 ml of water are added to the filtrate. The organic phase is separated off, washed once more with 10 ml of water, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 115 mg (41%) of the desired product; 1H-NMR(DMSO-(D6) δ: 8.39 (d, 1H), 7.48 (m, 2H), 7.22 (m, 2H), 7.17 (s, 1H), 7.03 (d, 1H), 3.35 (m, 1H), 2.43 (s, 3H), 1.39 (d, 6H).

Workup

  1. filtrationthe reaction mixture is filtered through a silica gel cartridge
  2. addition10 ml of water are added to the filtrate
  3. customThe organic phase is separated off
  4. washwashed once more with 10 ml of water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-f45645d5764e4cfbbdbf52bc73011a2f
Source dataset
uspto-grants-2015_12
Patent number
US09198426B2

Reaction notes

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