Methyl iodide → HCID 59354912, compound

HRID 1099440Notes

Reaction equation

HRID 1099440 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][NH:4][C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1)=[O:6].[H-].[Na+].[CH3:21]I>O1CCCC1>[CH3:21][N:4]([CH2:3][C:2]([F:1])([F:17])[F:18])[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59354914HCID 59354914, compound

Product 1

HCID 59354912HCID 59354912, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-[(2,2,2-trifluoroethyl)carbamoyl]nicotinate (3.0 g, 11.5 mmol) in tetrahydrofuran (15 mL) was added sodium hydride (60% suspension in mineral oil) (1.4 g) at ambient temperature. The reaction mixture was stirred for 1 h and methyl iodide (1.5 mL) was added. The reaction mixture was stirred over night and then quenched with water (20 mL). The mixture was extracted with ethyl acetate (3×50 mL) and the combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 1.72 g (61%) of the title compound; 1H NMR (400 MHz, CDCl3) δ ppm 8.43 (d, 1 H), 4.50 (q, 1 H), 4.23 (q, 1 H), 3.99 (s, 3 H), 3.24 (d, 3 H); MS (ESI) m/z 277[M+H+].

Workup

  1. stirringThe reaction mixture was stirred over night
  2. customquenched with water (20 mL)
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washthe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6774ef7d8ea34a80960a6dd8a74bf8c3
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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