Sodium Carbonate → HCID 22503484, compound

HRID 1007034Notes

Reaction equation

HRID 1007034 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([Cl:19])[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25](OB(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[ClH:19].[ClH:19].[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([C:25]3[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 147699944-Methoxyphenyl boric acid4×HCID 22502492HCID 22502492, compound

Product 1

HCID 22503484HCID 22503484, compoundYield 136.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(1-ethylpiperazin-4-yl)-2-chloroquinazoline(0.56 g), 4-methoxyphenylboric acid (0.46 g) tetrakistriphenylphosphinepalladium(0) (0.12 g), toluene (50 ml) and a 10% aqueous solution of sodium carbonate (30 ml) was vigorously stirred in nitrogen atmosphere at 100° C. for 1 hr. To the resulting mixture was additionally added 4-methoxyphenylboric acid (0.31 g), and the mixture was further stirred for 2 hr. To the resulting mixture was again added 4-methoxyphenylboric acid (0.31 g), and the mixture was further stirred for 1 hr. To the resulting mixture was further added 4-methoxyphenylboric acid (0.31 g), and the mixture was further stirred overnight. The resulting insoluble matters were filtered off, and then the organic layer was separated and extracted with 2N hydrochloric acid twice, followed by the addition of a 8N aqueous solution of sodium hydroxide to adjust the resulting mixture to pH 10. The resulting mixture was extracted with ethyl acetate twice. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system), to give 0.58 g of the free compound of the title compound as a pale yellow viscous oil.

Workup

  1. stirringthe mixture was further stirred for 1 hr
  2. stirringthe mixture was further stirred overnight
  3. filtrationThe resulting insoluble matters were filtered off
  4. customthe organic layer was separated
  5. extractionextracted with 2N hydrochloric acid twice
  6. additionfollowed by the addition of a 8N aqueous solution of sodium hydroxide
  7. extractionThe resulting mixture was extracted with ethyl acetate twice
  8. washThe extract was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated
  11. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system)

Sources & evidence

ORD record
ord-563dc79b18224e6bbdb73be2eac779c8
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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