1,1-Dichloroethane → HCID 178517775, compound

HRID 473127Notes

Reaction equation

HRID 473127 reaction equation
[F:1][C:2]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][N: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.ClC(Cl)C.Cl[Si](C)(C)C>>[F:1][C:2]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][N: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 3

HCID 63651,1-DichloroethaneHCID 6397ChlorotrimethylsilaneHCID 666106942-(2,2-Difluoro-2-(5-fluoropyridin-2-yl)acetamido)benzamide

Product 1

HCID 178517775HCID 178517775, compoundYield 91.8%

Conditions

Temperature
85 °C

Procedure

To 2-(2,2-difluoro-2-(5-fluoropyridin-2-yl)acetamido)benzamide (580 mg, 1.87 mmol) were added dichloroethane (15 mL) and TEA (11 mL, 75 mmol) followed by chlorotrimethylsilane (3.56 mL, 28 mmol) and the mixture was heated at 85° C. for 2-3 h. The mixture was concentrated to dryness and the residue was partitioned between saturated aq ammonium chloride and EtOAc. The organic layer was concentrated and the residue was purified by silica gel chromotography eluting with 0-10% MeOH/DCM to afford 2-(difluoro(5-fluoropyridin-2-yl)methyl)quinazolin-4-ol as a solid (500 mg, 91%). LC-MS (ESI) m/z 292 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue was partitioned between saturated aq ammonium chloride and EtOAc
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by silica gel chromotography
  5. washeluting with 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-5fdcdf9452fb4dffb757124b00887d84
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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