Bicarbonate Ion → HCID 135610098, compound

HRID 1272494Notes

Reaction equation

HRID 1272494 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].[C:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.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>[C:21]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][NH:6][C:5]3=[O:12])[C:22]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][CH:20]=1

Participants

11

Reactant 5

HCID 769Bicarbonate IonHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2545321-Naphthaleneboronic acidHCID 1354449056-bromoquinazolin-4-ol

Product 1

HCID 135610098HCID 135610098, compoundYield 62%

Reagents, catalysts & solvents 5

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

Procedure

To a solution of 6-bromo-3H-quinazolin-4-one (45.2 mg, 0.2 mmol) dissolved in 2 ml N,N-dimethylacetamide in a 20 ml vial, naphthalene-1-boronic acid (69.4 mg, 0.4 mmol) dissolved in 1 ml ethanol and potassium carbonate (30.5 mg, 0.22 mmol) dissolved in 1 ml water were added. Tripenylphosphine (5.27 mg, 0.02 mmol) and tris(dibenzylideneacetone)dipalladium (0) (3.6 mg, 4 umol) was 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. 32.9 mg product was obtained. Yield: 62%; 1H NMR (500 MHz, DMSO-d6): δ 7.52083–7.54615(m, 2H), 7.56877–7.58461(dd, J=6.88 Hz, 1H), 7.61224–7.64281(dd, J1=8.255 Hz, J2=8.285 Hz, 1H), 7.78775–7.804 (d, J=8.125 Hz, 1H), 7.82384–7.84054(d, J=8.35 Hz, 1H), 7.93472–7.95545(dd, J1=8.365 Hz, J2=2 Hz, 1H), 8.00847–8.02533(d, J=8.43 Hz, 1H), 8.03829–8.05347(d, J=7.59 Hz, 1H), 8.15915–8.16300(d, J=1.925 Hz, 1H), 8.19218 (s, 1H); ESI-MS: m/z 273 (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-4f9dbda6f84543f7bcc7bcd2489c255d
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

Loading…