Bromide ion → HCID 67007388, compound

HRID 2240510Notes

Reaction equation

HRID 2240510 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[Br-]>CN(C=O)C.C(OCC)(=O)C>[CH2:8]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 59674890HCID 59674890, compound

Product 1

HCID 67007388HCID 67007388, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of tert-butyl 5,6-dihydro-4-(3-hydroxyphenyl)pyridine-1(2H)-carboxylate (crude, 100 mg) and potassium carbonate (300 mg) in DMF was added bnezyl bromide (60 μL) at room temperature. The resulting mixture was stirred at 80° C. for 16 h. The mixture was cooled down, diluted with ethyl acetate, washed with water, brine, dried and concentrated. The product (60 mg) was purified by combiflash using hexane/ethyl acetate (max. EtOAc 10%) to afford tert-butyl 4-(3-(benzyloxy)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate which was then converted to the final compound using procedures analogous to those for example 1. MS(ESI): (M+H)+=462.2

Workup

  1. temperatureThe mixture was cooled down
  2. washwashed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe product (60 mg) was purified by combiflash

Sources & evidence

ORD record
ord-ba365a794407430680766ea3eacb49ed
Source dataset
uspto-grants-2010_05
Patent number
US07723349B2

Reaction notes

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