Bicarbonate Ion → HCID 135610093, compound

HRID 1272491Notes

Reaction equation

HRID 1272491 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=[O:12].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=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>[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=[O:12]

Participants

11

Reactant 5

HCID 769Bicarbonate IonHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 5833222,6-Dimethylphenylboronic acidHCID 1354449056-bromoquinazolin-4-ol

Product 1

HCID 135610093HCID 135610093, compoundYield 40.1%

Reagents, catalysts & solvents 5

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

Procedure

To a solution of 6-bromo-3H-quinazolin-4-one (43.1 mg, 0.1915 mmol) dissolved in 2 ml N,N-dimethylacetamide in a 20 ml vial, 2,6-dimethylphenylboronic acid (114.9 mg, 0.76 mmol) dissolved in 1 ml ethanol and potassium carbonate (26.7 mg, 0.193 mmol) dissolved in 1 ml water were added. Triphenylphosphine (5 mg, 0.019 mmol) and tris(dibenzylideneacetone)dipalladium(0) (3.5 mg, 3.8 umol) were added to the mixture which refluxed overnight. The crude product was poured into 50 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. 19.2 mg product was obtained. Yield: 40%; 1H NMR (500 MHz, DMSO-d6): δ 1.96741(s, 6H), 7.114769–7.16307(d, J=7.69 Hz, 2H), 7.19260–7.22248(dd, J1=8.62 Hz, J2=6.31 Hz 1H), 7.60434–7.62503(dd, J1=8.335 Hz, J2=1.97 Hz, 1H), 7.75179–7.76829(d, J=8.25 Hz, 1H), 7.81882–7.82258(d, J=1.88 Hz, 1H), 8.17882 (s, 1H); ESI-MS: m/z 251 (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-e2e2eeb3a1364f0383569c3e810dfe8b
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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