Potassium Carbonate → HCID 69511592, compound

HRID 969689Notes

Reaction equation

HRID 969689 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br)[CH3:2].[N:13]1[C:22]2[C:17](=[CH:18][C:19]([NH2:23])=[CH:20][CH:21]=2)[CH:16]=[N:15][CH:14]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:23][C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[N:13]=[CH:14][N:15]=[CH:16]2)[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80186Ethyl 2-bromobenzoateHCID 589288quinazolin-6-amineHCID 634876Binap, (A+-)-

Product 1

HCID 69511592HCID 69511592, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-bromo-benzoic acid ethyl ester (7.9 g), quinazolin-6-ylamine (5.0 g), Pd(OAc)2 (387 mg), BINAP (714 mg), and K2CO3 (26 g) in toluene (100 mL was heated at reflux for 12 h. The mixture was diluted with EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified with flash chromatography (SiO2 50% EtOAc/hexane) to obtain 2-(quinazolin-6-ylamino)-benzoic acid ethyl ester. MS (ES+): 294.0 (M+H)+. Calc'd for C17H15N3O2: 293.32.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified with flash chromatography (SiO2 50% EtOAc/hexane)

Sources & evidence

ORD record
ord-55b1210a0d0043389388985c9a724d53
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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