Methyl iodide → HCID 54671268, compound

HRID 1404793Notes

Reaction equation

HRID 1404793 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]3[N:16]([CH2:19][C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[N:26]=[CH:25][CH:24]=[CH:23]5)[N:17]=[N:18][C:13]3=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[CH2:30][OH:31].[CH3:32]I>CN(C=O)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]3[N:16]([CH2:19][C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[N:26]=[CH:25][CH:24]=[CH:23]5)[N:17]=[N:18][C:13]3=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[CH2:30][O:31][CH3:32]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54670140HCID 54670140, compound

Product 1

HCID 54671268HCID 54671268, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.010 g, 0.259 mmol) was added at 0° C. to a solution of example 16 (0.100 g, 0.259 mmol) in DMF (1 ml) and stirred for 30 min. Methyl iodide (0.073 g, 0.518 mmol) was added and the reaction mixture was warmed to RT. After 12 h, the reaction mixture was poured into ice-cold water and extracted with ethyl acetate, washed with brine, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography with methanol:dichloromethane to afford the title compound as an off-white solid (0.033 g, 32%). M.P.: 200-201° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.88 (dd, J=4.2, 1.7 Hz, 1H), 8.68 (d, J=8.8 Hz, 1H), 8.37 (d, J=8.4 Hz, 1H), 8.18 (d, J=8.8 Hz, 1H), 8.11-8.00 (m, 4H), 7.83 (dd, J=8.7, 1.9 Hz, 1H), 7.61 (t, J=7.7 Hz, 1H), 7.53 (dd, J=8.4, 4.2 Hz, 1H), 6.22 (s, 2H), 4.53 (s, 2H), 3.33 (s, 3H).

Workup

  1. waitAfter 12 h
  2. additionthe reaction mixture was poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-be964b1a9c6043e9a3fa9898edfe9def
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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