Sodium Carbonate → HCID 22648055, compound

HRID 394189Notes

Reaction equation

HRID 394189 reaction equation
Br[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:6](=[O:23])[N:7]2[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22].C([O-])([O-])=O.[Na+].[Na+].[Cl:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1B(O)O.C(O)C.O>C1(C)C=CC=CC=1.C(OCC)(=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>[Cl:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:6](=[O:23])[N:7]2[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 19096565Water ethanolHCID 226481455-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one

Product 1

HCID 22648055HCID 22648055, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

1.07 g of 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one (1.99 mmol) were dissolved in 26 mL of toluene. Na2CO3 (1.26 g, 11.9 mmol), 2-chlorophenylboronic acid (934 mg, 5.97 mmol), and ethanol/water (6.4 mL:6.4 mL) were added under argon followed by Pd(Ph3P)4 (115 mg, 0.0995 mmol). The resulting reaction mixture was stirred at 100° C. for ca.4 h, cooled to rt, diluted with 150 mL of ethyl acetate, washed with 2×100 mL of saturated aqueous NaHCO3 and 100 mL of brine, dried over Na2SO4, and concentrated under reduced pressure. The product was purified by flash chromatography on Biotage 40M column, eluting with 80:20 hexanes-acetone to yield 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one. Mass spectrum (ESI) 568.1 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. temperature4 h, cooled to rt
  3. washwashed with 2×100 mL of saturated aqueous NaHCO3 and 100 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by flash chromatography on Biotage 40M column
  7. washeluting with 80:20 hexanes-acetone

Sources & evidence

ORD record
ord-2f243b4285634dbbadef30547f79f833
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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