Chlorotrimethylsilane → HCID 178517771, compound

HRID 1424397Notes

Reaction equation

HRID 1424397 reaction equation
[F:1][C:2]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH2:10])=[O:9])=O.Cl[Si](C)(C)C>ClCCCl>[F:1][C:2]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:3]1[N:10]=[C:8]([OH:9])[C:7]2[C:6](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 666093272-(2,2-Difluoro-2-(4-fluorophenyl)acetamido)benzamide

Product 1

HCID 178517771HCID 178517771, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-(2,2-difluoro-2-(4-fluorophenyl)acetamido)benzamide (0.95 g, 3.08 mmol) in DCE (25 mL), TEA (17.2 mL, 0.123 mol) and chlorotrimethylsilane (5.84 mL, 0.0462 mol) were added at rt. The reaction mixture was stirred at 85° C. overnight. After cooling to rt, the solid was filtered and the filtrate was concentrated to dryness. The residue was purified on a silica gel column, using DCM/MeOH as eluent. 2-(Difluoro(4-fluorophenyl)methyl)quinazolin-4-ol was obtained as an off white solid (0.668 g, 75%). 1H NMR (300 MHz, DMSO-d6) δ 7.39 (t, 2H), 7.62 (m, 1H), 7.78-7.71 (m, 3H), 7.84 (m, 1H), 8.16 (m, 1H), 13.11 (s, 1H).

Workup

  1. temperatureAfter cooling to rt
  2. filtrationthe solid was filtered
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-0a0886ef323b477e8e18bc2cca419e82
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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