8-Nitro-4-(3-(trifluoromethyl)phenoxy)quinazoline → HCID 71680391, compound

HRID 1469728Notes

Reaction equation

HRID 1469728 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][N:10]=[C:9]2[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)([O-])=O>CCOC(C)=O.[Pd]>[F:24][C:21]([F:22])([F:23])[C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][C:9]1[C:8]2[C:13](=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=2)[N:12]=[CH:11][N:10]=1

Participants

4

Reactant 1

HCID 716803958-Nitro-4-(3-(trifluoromethyl)phenoxy)quinazoline

Product 1

HCID 71680391HCID 71680391, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-nitro-4-(3-(trifluoromethyl)phenoxy)quinazoline (400 mg, 1.19 mmol) in EtOAc (5 mL) was added 10% Pd on C (200 mg) and the suspension was hydrogenated in a Parr apparatus for 1 h at 20 psi. Then the reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified by column chromatography using 5% EtOAc in CHCl3 to afford 300 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.60 (s, 1H), 7.79 (s, 1H), 7.75-7.71 (m, 3H), 7.47-7.44 (m, 2H), 7.11 (d, J=6.3 Hz, 1H), 6.07 (s, 2H); MS (m/z): 305.19 (M+H)+.

Workup

  1. filtrationThen the reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4d3ac43f6d3e4669bf6c0d76e091a019
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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