HCID 57958802, compound → HCID 59359756, compound

HRID 1187277Notes

Reaction equation

HRID 1187277 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH2:19]([Mg]Br)[CH2:20][CH3:21]>C1COCC1.CCOCC>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[N:5]=[CH:4][N:3]=[C:2]3[CH2:19][CH2:20][CH3:21])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 57958802HCID 57958802, compoundHCID 178455851HCID 178455851, compound

Product 1

HCID 59359756HCID 59359756, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-6-(4-fluorophenyl)-quinazoline (258 mg, 1 mmol) and Fe(acac)3 (17 mg, 0.05 mmol) in THF (5 ml) was added n-propyl magnesium bromide (600 ul of 2M THF solution). The reaction was stirred at RT for 1 hour at RT then diluted with ether (5 ml) and quenched with 3 drops 2N HCl. The mixture was further diluted with ether and extracted with H2O. The aqueous layer was neutralized with a saturated aqueous NaHCO3 solution and extracted 3× with ether. The combined organics were washed once with NaHCO3 and once with a saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by column chromatography on SiO2 using EtOAc/hex (10-30% EtOAc) to give the title compound (115 mg, 43% yield) which was characterized by mass spectrum as follows: (m/z): 267 ([M+H]) 100).

Workup

  1. customquenched with 3 drops 2N HCl
  2. additionThe mixture was further diluted with ether
  3. extractionextracted with H2O
  4. extractionextracted 3× with ether
  5. washThe combined organics were washed once with NaHCO3 and once with a saturated aqueous NaCl solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by column chromatography on SiO2

Sources & evidence

ORD record
ord-14e1f3e979dc486084df6946477c2993
Source dataset
uspto-grants-2014_03
Patent number
US08673929B2

Reaction notes

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