Bicarbonate Ion → HCID 135610094, compound

HRID 1272492Notes

Reaction equation

HRID 1272492 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].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][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>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][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 33782712-Chloro-6-methoxyphenylboronic acidHCID 1354449056-bromoquinazolin-4-ol

Product 1

HCID 135610094HCID 135610094, compoundYield 24.3%

Reagents, catalysts & solvents 5

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

Procedure

To a solution of 6-bromo-3H-quinazolin-4-one (38.9 mg, 0.1728 mmol) dissolved in 2 ml N,N-dimethylacetamide in a 20 ml vial, 2-chloro-6-methoxy-phenylboronic acid (128.88 mg, 0.6914 mmol) dissolved in 1 ml ethanol and potassium carbonate (26.28 mg, 0.19 mmol) dissolved in 1 ml water were added. Triphenylphosphine (4.5 mg, 0.017 mmol) and tris(dibenzylideneacetone)dipalladium(0) (3.2 mg, 3.5 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. 3.4 mg product was obtained. Yield: 24.3%; 1H NMR (500 MHz, DMSO-d6): δ 3.70812(s, 3H), 7.13816–7.15637 (dd, J1=7.945 Hz, J2=0.32 Hz, 1H), 7.18430–7.20184 (dd, J1=7.85 Hz, J2=0.92 Hz 1H), 7.40806–7.44074 (dd, J1=8.205 Hz, J2=8.135 Hz, 1H), 7.66531–7.68611 (dd, J1=8.305 Hz, J2=2.04 Hz, 1H), 7.71531–7.73209 (d, J=8.39 Hz, 1H), 7.92946–7.93334 (d, J=1.94 Hz, 1H), 8.16800 (s, 1H); ESI-MS: m/z 287 (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-e3546ea1262b4d94bf0f2513ee78e40e
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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