Bicarbonate Ion → HCID 18455729, compound

HRID 1272497Notes

Reaction equation

HRID 1272497 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([C:12](=[O:16])[CH2:13][CH2:14][OH:15])[C:5]2=[O:17].[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-]>CN(C)C(=O)C.C(O)C.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)Cl>[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([C:12](=[O:16])[CH2:13][CH2:14][OH:15])[C:5]2=[O:17]

Participants

11

Reactant 5

HCID 769Bicarbonate IonHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 5833222,6-Dimethylphenylboronic acidHCID 18455748HCID 18455748, compound

Product 1

HCID 18455729HCID 18455729, compoundYield 49%

Reagents, catalysts & solvents 5

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 6-Bromo-3-(3-hydroxy-propionyl)-3H-quinazolin-4-one (9.8 mg, 0.033 mmol) dissolved in 1 ml N,N-dimethylacetamide in a 20 ml vial, 2,6-dimethylphenyl boronic acid (9.89 mg, 0.066 mmol) dissolved in 0.5 ml ethanol and potassium carbonate (5 mg, 0.036 mmol) dissolved in 0.5 ml water were added. Triphenylphosphine (0.87 mg, 3.3 umol) and tris(dibenzylideneacetone)dipalladium(0) (0.6 mg, 0.6 umol) were added to the mixture which refluxed overnight. The crude product was poured into 5 ml saturated bicarbonate solution and methylene chloride was used to extract the product. Solvent in the organic phase was removed under vacuum. The resulted residue was purified by preparative HPLC. 5.2 mg product was obtained. Yield: 49%; 1H NMR (500 MHz, DMSO-d6): δ 1.96247(s, 6H), 2.76290–2.79002(t, J=6.805 Hz, 2H), ), 4.15954–4.18664 (t, J=6.785 Hz, 2H), 7.14682–7.7.1621(d, J=7.64 Hz, 1H), 7.19338–7.21062(dd, J1=8.62 Hz, J2=6.41 Hz, 1H), 7.60532–7.62604(dd, J1=8.365 Hz, J2=2.03 Hz, 1H), 7.75204–7.76861 (d, J=8.285 Hz, 1H), 7.84928–7.85312(d, J=1.92 Hz, 1H), 8.41195(s, 1H); ESI-MS: m/z 323 (M++1)

Workup

  1. additionwere added
  2. temperaturerefluxed overnight
  3. extractionto extract the product
  4. customSolvent in the organic phase was removed under vacuum
  5. customThe resulted residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-03536448dd4b4ba48a4833b5a741048c
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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