Methyl iodide → HCID 66580942, compound

HRID 1521845Notes

Reaction equation

HRID 1521845 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:13]([C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:24])=[N:14][N:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=1)(=[O:10])=[O:9].[H-].[Na+].IC.[CH2:35](Cl)Cl>C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH3:35])[C:12]1[C:13]([C:23]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)=[O:24])=[N:14][N:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=1)(=[O:9])=[O:10]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 66581050HCID 66581050, compound

Product 1

HCID 66580942HCID 66580942, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-N-[3-(morpholin-4-ylcarbonyl)-1-phenyl-1H-pyrazol-4-yl]benzenesulfonamide (30 mg; 0.06 mmol; 1.00 eq.) in THF (6 mL) is added sodium hydride (3 mg; 0.07 mmol; 1.20 eq.) and the reaction is stirred for 10 min before the addition of iodomethane (4 μL; 0.07 mmol; 1.10 eq.). After 12 h, DCM is added to the reaction mixture, ished with water (×2) and dried the organic phase over MgSO4 give 30 mg (97%) of the title compound as a white solid. 1H NMR (DMSO) δ 8.64 (s, 1H), 7.93-7.86 (m, 2H), 7.80-7.73 (m, 2H), 7.62-7.47 (m, 4H), 7.41-7.32 (m, 1H), 3.65-3.51 (m, 6H), 3.48-3.42 (m, 2H), 3.35 (s, 3H). HPLC (max plot) 89.7%; Rt 3.98 min. MS (ESI+): 507.2.

Workup

  1. dry with materialdried the organic phase over MgSO4

Sources & evidence

ORD record
ord-387abd6fa43d406c85541afc4264ae86
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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