Sodium Iodide → 3-(4-(benzyloxy)phenylsulfonyl)-N-mesityl-6-methylpyridin-2-amine

HRID 1796329Notes

Reaction equation

HRID 1796329 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][CH:3]=1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.CCOC(C)=O>[CH2:28]([O:27][C:24]1[CH:23]=[CH:22][C:21]([S:18]([C:5]2[C:6]([NH:8][C:9]3[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=3[CH3:17])=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:20])=[O:19])=[CH:26][CH:25]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 112112464-[6-Methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenol

Product 1

HCID 112252363-(4-(benzyloxy)phenylsulfonyl)-N-mesityl-6-methylpyridin-2-amineYield 92.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[6-Methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenol from Example 10 (300 mg, 0.78 mmol), benzyl bromide (0.10 mL, 0.84 mmol), K2CO3 (129 mg, 0.93 mmol) and NaI (20 mg, 0.13 mmol) was heated at reflux in acetonitrile (5 mL) for 15 h. Then it was diluted with EtOAc (15 mL), filtered through florisil and the filtrate was stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent to give the product as a solid (340 mg), mp 158–160° C. mass spec. (AP+): m/z 473 (M+1).

Workup

  1. filtrationfiltered through florisil
  2. customThe residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent

Sources & evidence

ORD record
ord-dd859d8d170f4ceebe005eadf0625f91
Source dataset
uspto-grants-2006_04
Patent number
US07030145B2

Reaction notes

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