Bicarbonate Ion → HCID 135610092, compound

HRID 1272493Notes

Reaction equation

HRID 1272493 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]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[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]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[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 2921842,4,6-Trimethylbenzeneboronic acidHCID 1354449056-bromoquinazolin-4-ol

Product 1

HCID 135610092HCID 135610092, compoundYield 40%

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, 2,4,6-trimethylphenylboronic 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 265 (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-ac5b7452ac7e43f0880c3a56b06c0081
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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