Ethyl 4-chloroquinazoline-2-carboxylate → (4-Chloroquinazolin-2-yl)(3-fluorophenyl)methanone

HRID 1801878Notes

Reaction equation

HRID 1801878 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14]CC)=O)[N:3]=1.[F:17][C:18]1[CH:19]=[C:20]([Mg]Br)[CH:21]=[CH:22][CH:23]=1>C1COCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([F:17])[CH:23]=2)=[O:14])[N:3]=1

Participants

4

Reactant 2

HCID 3477840Ethyl 4-chloroquinazoline-2-carboxylateHCID 178505773HCID 178505773, compound

Product 1

HCID 86649047(4-Chloroquinazolin-2-yl)(3-fluorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a suspension of ethyl 4-chloroquinazoline-2-carboxylate (237 mg, 1 mmol) in THF (5 mL) was added dropwise a 1M solution of 3-fluorophenylmagnesium bromide in THF (2 mL, 2 mmol) at −20° C. The reaction mixture was stirred at −20° C. for 4 h. The mixture was quenched by adding 0.5 N HCl solution (5 mL) and the biphasic mixture was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine and dried over MgSO4. (4-chloroquinazolin-2-yl)(3-fluorophenyl)methanone was obtained as a yellow solid (190 mg, 66%). LC-MS (ESI) m/z 287 (M+H)+.

Workup

  1. customThe mixture was quenched
  2. additionby adding 0.5 N HCl solution (5 mL)
  3. extractionthe biphasic mixture was extracted with EtOAc (2×10 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-92e8940791794b3e96e9bcd58ec48e68
Source dataset
uspto-grants-2013_01
Patent number
US08349851B2

Reaction notes

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