Methyl iodide → HCID 67419119, compound

HRID 1429357Notes

Reaction equation

HRID 1429357 reaction equation
[CH2:1]([CH:8]1[CH2:15][NH:14][C:13](=[O:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[CH2:10][N:9]1[S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])(=[O:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:34]I>CN(C=O)C>[CH2:1]([CH:8]1[CH2:15][N:14]([CH3:34])[C:13](=[O:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[CH2:10][N:9]1[S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])(=[O:23])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67419107HCID 67419107, compound

Product 1

HCID 67419119HCID 67419119, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 2g (120 mg, 0.28 mmol) in DMF (15 mL) at 10° C., NaH (60% in mineral oil; 13 mg, 0.33 mmol) was added in portions. The mixture was stirred for an additional 45 min and then MeI (116 mg, 0.82 mmol) was added dropwise. The resulting mixture was stirred at 10° C. for 30 min and warmed to rt overnight. The reaction was quenched with water (30 mL) and extracted with EA (40 mL). The organic layer was washed with brine (2×20 mL) and dried over anhydrous Na2SO4. Concentration in vacuo and purification by prep-TLC (PE:EA=1:1) gave compound 2h as a white solid (110 mg, 89% yield). 1H-NMR (400 MHz, CD3OD) δ 7.82 (dd, 1H, J=8.0, 1.6 Hz), 7.51 (t, J=8.8 Hz, 1H), 7.36-7.23 (m, 4H), 7.05-6.99 (m, 5H), 6.72-6.70 (m, 2H), 5.41 (d, J=18.8 Hz, 1H), 4.55 (d, J=19.2 Hz, 1H), 4.10 (m, 1H), 3.82 (s, 3H), 3.28 (dd, J=14.4, 11.6 Hz, 1H), 2.98 (dd, J=15.2, 4.8 Hz, 1H), 2.86 (s, 3H), 2.61 (dd, J=12.8, 9.6 Hz, 1H), 2.47 (dd, J=12.8, 4.8 Hz, 1H). MS (ESI+) m/z: 451 [M+H]+

Workup

  1. stirringThe resulting mixture was stirred at 10° C. for 30 min
  2. customThe reaction was quenched with water (30 mL)
  3. extractionextracted with EA (40 mL)
  4. washThe organic layer was washed with brine (2×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationConcentration
  7. customin vacuo and purification by prep-TLC (PE:EA=1:1)

Sources & evidence

ORD record
ord-ec4df04afca14bef86ba0420b98649d6
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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