Methyl iodide → HCID 44192802, compound

HRID 1404076Notes

Reaction equation

HRID 1404076 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]2[C:12]=1[C:13]([CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[CH:14][NH:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:26]I>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]2[C:12]=1[C:13]([CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])=[CH:14][N:15]2[CH3:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10805071HCID 10805071, compound

Product 1

HCID 44192802HCID 44192802, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

At 0° C., NaH (2 eq) was added to a solution of 1 eq of compound 1-7c in DMF. After 30 min, a solution of 0.1 M methyl iodide in DMF was added slowly over 30 min, and then the reaction mixture was allowed to warm to 25° C. and stirred at that temperature for 1 h. After standard workup, the brown oil residue was purified by column chromatography, eluting with CH2Cl2/2% NH4OH. A brown oil (1-8c) was obtained in 84% yield. 1H NMR (CDCl3-d, 300 MHz) δ (ppm) 2.13 (s, 6H), 2.50-2.56 (m, 2H), 2.95-3.01 (m, 2H), 3.89 (d, 3H, J=1.9), 5.13 (s, 2H), 6.29 (dd, 1H, J=8.5, 2.8), 6.67 (dd, 1H, J=8.5, 12.1), 6.69 (s, 1H), 7.29-7.40 (m, 3H), 7.45-7.48 (m, 2H). APCI [M+1]: 327.2.

Workup

  1. customAfter standard workup, the brown oil residue was purified by column chromatography
  2. washeluting with CH2Cl2/2% NH4OH

Sources & evidence

ORD record
ord-ee88aedbe2c34d8bbef3cefdb770c7f0
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

Loading…