Potassium Phosphate, Tribasic → HCID 59511774, compound

HRID 1157465Notes

Reaction equation

HRID 1157465 reaction equation
[CH:1]([NH:4][C:5](=[O:35])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13](B3OC(C)(C)C(C)(C)O3)[CH:14]=2)[N:9]=[C:8]1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=1)([CH3:3])[CH3:2].Br[C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[F:45])[CH:40]=[O:41].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:45][C:44]1[CH:43]=[CH:42][C:39]([CH:40]=[O:41])=[CH:38][C:37]=1[C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=1)[N:7]([CH2:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:35])[C:16]2=[O:17]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 59511778HCID 59511778, compound

Product 1

HCID 59511774HCID 59511774, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-isopropyl-2-[2-(3-methoxyphenyl)-4-oxo-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-4H-quinazolin-3-yl]acetamide (70 mg, 0.15 mmol) in DMF (3 mL) was added 3-bromo-4-fluorobenzaldehyde (70 mg, 0.34 mmol), followed by tetrakis(triphenylphosphine)palladium (Pd[P(C6H5)3]4) (24 mg, 0.02 mmol) and 2M K3PO4 (aq.) (0.38 mL, 0.76 mmol). The mixture was heated at 80° C. under argon for 20 h, then cooled to room temperature and DMF evaporated in vacuo. The crude product was purified by preparative thin layer chromatography on silica gel with methanol:dichloromethane (1:9, v/v) as eluent to provide 2-[6-(2-fluoro-5-formylphenyl)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (19.3 mg, 0.04 mmol, 27% yield).

Workup

  1. temperaturecooled to room temperature
  2. customDMF evaporated in vacuo
  3. customThe crude product was purified by preparative thin layer chromatography on silica gel with methanol:dichloromethane (1:9, v/v) as eluent

Sources & evidence

ORD record
ord-dccebf77f4f349b09211fd16565a7d4a
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

Loading…