Chlorotrimethylsilane → HCID 86609784, compound

HRID 222310Notes

Reaction equation

HRID 222310 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([C:18]([O:22]COCCOC)=[C:19]([F:21])[F:20])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.Cl[Si](C)(C)C.C(=O)(O)[O-].[Na+]>CO.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([C:18](=[O:22])[CH:19]([F:20])[F:21])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 67413502HCID 67413502, compound

Product 1

HCID 86609784HCID 86609784, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 3-chloro-7-{2,2-difluoro-1-[(2-methoxyethoxy)methoxy]vinyl}-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (50 mg, 0.12 mmol) in a mixture of methanol (0.6 mL) and dichloromethane (0.6 mL) was added chlorotrimethylsilane (0.08 mL, 0.61 mmol). The mixture was allowed to warm to ambient temperature and stirred overnight. The mixture was then poured into an aqueous sodium bicarbonate solution and extracted with ethyl acetate three times. The combined organics were dried over magnesium sulfate, filtered, concentrated in vacuo, and purified via flash chromatography (silica, 0-60% ethyl acetate/hexanes) to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 8.84 (d, 1H), 8.52 (d, 1H), 8.41 (s, 1H), 7.93 (dd, 1H), 7.76 (d, 1H), 7.42 (d, 1H), 7.33 (d, 1H), 5.79 (t, 1H). LRMS (APCI) calc'd for (C16H9ClF2NO2) [M+H]+, 320.0; found 320.0.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified via flash chromatography (silica, 0-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a14266265807410c9d96706cd63b6e03
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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