Potassium Carbonate → HCID 67071507, compound

HRID 874292Notes

Reaction equation

HRID 874292 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.[CH3:17][O:18][C:19](=[O:43])/[CH:20]=[CH:21]/[C:22]1[CH:23]=[C:24]2[C:39](=[CH:40][CH:41]=1)[O:38][C:27]1([CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28]1)[CH2:26][C:25]2=[O:42]>C(#N)C>[CH3:17][O:18][C:19](=[O:43])/[CH:20]=[CH:21]/[C:22]1[CH:23]=[C:24]2[C:39](=[CH:40][CH:41]=1)[O:38][C:27]1([CH2:30][N:29]([CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[CH2:28]1)[CH2:26][C:25]2=[O:42]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5731534-Fluorophenethyl bromideHCID 67071422HCID 67071422, compound

Product 1

HCID 67071507HCID 67071507, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

K2CO3 (285 mg, 2.06 mmol) and 1-(2-bromoethyl)-4-fluorobenzene (0.43 ml, 3.1 mmol) were added to a suspension of Intermediate 4 (320 mg, 1.04 mmol) in acetonitrile (30 ml) and the mixture was stirred at 70° C. for 54 h. The solvent was evaporated and the residue was partitioned between water and DCM. The organic phase was dried over Na2SO4, filtered and evaporated. The crude residue was purified by column chromatography on silica gel (eluent:petroleum ether:EtOAc 6:4) to give (E)-3-{1′-[2-(4-fluoro-phenyl)-ethyl]-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl}-acrylic acid methyl ester (120 mg) as a brown oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between water and DCM
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by column chromatography on silica gel (eluent:petroleum ether:EtOAc 6:4)

Sources & evidence

ORD record
ord-07f9282fd6a846e3a49ce4b20fc99f3b
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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