Dimethylformamide → HCID 17984485, compound

HRID 1181123Notes

Reaction equation

HRID 1181123 reaction equation
C([O:5][C:6](=[O:32])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30]Br)(C)(C)C.[F:33][C:34]([F:43])([F:42])[C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1.CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CCOCC>[CH3:23][C:22]1[O:21][C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:19][C:18]=1[CH2:17][CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][C:6]([OH:5])=[O:32])=[C:10]([CH2:30][O:41][C:38]2[CH:39]=[CH:40][C:35]([C:34]([F:33])([F:42])[F:43])=[CH:36][CH:37]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 678744-(Trifluoromethyl)phenolHCID 58979125HCID 58979125, compound

Product 1

HCID 17984485HCID 17984485, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

General procedure for parallel synthesis using the DynaVac Carousel apparatus. A 50 mL glass tube with screw cap and nitrogen inlet was charged with 3-{2-bromomethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid tert-butyl ester (0.040 g, 0.080 mmol), 4-trifluoromethylphenol (0.019 g 0.12 mmol), anhydrous DMF (0.5 mL), and then cesium carbonate (0.039 g, 0.12 mmol). The mixture was stirred at ambient temperature for 16 h. MS analysis of the reaction indicated formation of the intermediate ester product [MS (ES) m/e 582 (M+1)]. The reaction mixture was poured into ether (30 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated. The residue was diluted with CH2Cl2 (1 mL) and trifluroacetic acid (0.25 mL) was added. The mixture was stirred at ambient temperature for 1.5 h and was concentrated. The crude product mixture was purified by mass-directed reverse phase HPLC to provide the title compound (0.045 g, 64%). MS (ES) m/e 526 (M+1).

Workup

  1. customGeneral procedure for parallel synthesis
  2. customA 50 mL glass tube with screw cap
  3. washThe organic layer was washed with brine (2×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. additionThe residue was diluted with CH2Cl2 (1 mL) and trifluroacetic acid (0.25 mL)
  7. additionwas added
  8. stirringThe mixture was stirred at ambient temperature for 1.5 h
  9. concentrationwas concentrated
  10. customThe crude product mixture was purified by mass-directed reverse phase HPLC

Sources & evidence

ORD record
ord-7ff285a9ade049ce89c9de7313b20d05
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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