Methyl iodide → 2-Methyl-propane-2-sulfinic acid [(2-amino-5-bromo-phenyl)-(4-chloro-phenyl)-methyl]-methyl-amide

HRID 1497715Notes

Reaction equation

HRID 1497715 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH:9]([NH:17][S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1.CI.[CH2:26](N(CC)CC)C>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH:9]([N:17]([CH3:26])[S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 1176205182-Methyl-propane-2-sulfinic acid [(2-amino-5-bromo-phenyl)-(4-chloro-phenyl)-methyl]-amide

Product 1

HCID 1176191492-Methyl-propane-2-sulfinic acid [(2-amino-5-bromo-phenyl)-(4-chloro-phenyl)-methyl]-methyl-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-Methyl-propane-2-sulfinic acid [(2-amino-5-bromo-phenyl)-(4-chloro-phenyl)-methyl]-amide (9.73 g, 0.024 mmol) solved in 150 mL DMF is added LiHNDS (1.06M, 24.5 mL) at −30° C. After 1 h, methyl iodide (3.4 g, 0.024 mol) and triethylamine (33.5 mL, 0.24 mol) is added. The mixture is stirred at RT for 2 h. The mixture is then quenched with H2O, extracted with CH3O(CH3)3, dried over Na2SO4, concentrated. This produces the desired compound.

Workup

  1. additionis added LiHNDS (1.06M, 24.5 mL) at −30° C
  2. customThe mixture is then quenched with H2O
  3. extractionextracted with CH3O(CH3)3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-501e5831f10b4bbca838e3334299e612
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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