Chlorotrimethylsilane → HCID 178517771, compound

HRID 625738Notes

Reaction equation

HRID 625738 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-b145907829844dbd89d7c39b436f4c85
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

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