Trimethylsilyl iodide → HCID 67008298, compound

HRID 1944609Notes

Reaction equation

HRID 1944609 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]4[CH:22]=[CH:21][C:20]([C:23]5[CH:24]=[N:25][C:26]([O:29]C)=[CH:27][CH:28]=5)=[CH:19][C:17]4=3)[CH:12]=[CH:11][C:10]2=[O:31])[CH:5]=[CH:6][C:7]=1[F:8].[Si](I)(C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]4[CH:22]=[CH:21][C:20]([C:23]5[CH:28]=[CH:27][C:26](=[O:29])[NH:25][CH:24]=5)=[CH:19][C:17]4=3)[CH:12]=[CH:11][C:10]2=[O:31])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 67008365HCID 67008365, compound

Product 1

HCID 67008298HCID 67008298, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of compound 7.0 1-(3-chloro-4-fluorophenyl)-9-(6-methoxypyridin-3-yl)benzo[h][1,6]naphthyridin-2(1H)-one (21 mg, 0.05 mmol, 1 equiv.) in CH2Cl2(2 mL) at room temperature was added TMSI (70 μL, 0.5 mmol, 10 equiv.). The resulting solution was stirred at 50° C. for 48 h before being cooled to room temperature and quenched with Na2CO3 (sat. 2 mL). After separation, the organic phase was dried over Na2SO4 and evaporated under vacuum. The residue was diluted with DMF (2 mL) and purified via preparative LC-MS (CH3CN: H2O) to afford the desired product 7.1 1-(3-chloro-4-fluorophenyl)-9-(6-oxo-1,6-dihydropyridin-3-yl)benzo[h][1,6]naphthyridin-2(1H)-one (3 mg). LC-MS (M+H): 417.07

Workup

  1. temperaturebefore being cooled to room temperature
  2. customquenched with Na2CO3 (sat. 2 mL)
  3. customAfter separation
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customevaporated under vacuum
  6. additionThe residue was diluted with DMF (2 mL)
  7. custompurified via preparative LC-MS (CH3CN: H2O)

Sources & evidence

ORD record
ord-f3f5ae95a2454ac9873dcd511ecb4381
Source dataset
uspto-grants-2013_03
Patent number
US08394818B2

Reaction notes

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