Dichloromethane → t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate

HRID 68604Notes

Reaction equation

HRID 68604 reaction equation
C(Cl)Cl.[C:4]([C:6]1[CH:7]=[C:8]([C:13]2[CH:27]=[C:26]([CH2:28][NH:29][CH3:30])[CH:25]=[CH:24][C:14]=2[O:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:9]=[C:10]([F:12])[CH:11]=1)#[N:5].CCN(CC)CC.[F:38][C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1>O>[C:4]([C:6]1[CH:7]=[C:8]([C:13]2[CH:27]=[C:26]([CH2:28][N:29]([CH3:30])[S:45]([C:42]3[CH:43]=[CH:44][C:39]([F:38])=[CH:40][CH:41]=3)(=[O:47])=[O:46])[CH:25]=[CH:24][C:14]=2[O:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:9]=[C:10]([F:12])[CH:11]=1)#[N:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 67528259HCID 67528259, compound

Product 1

HCID 67528467t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetateYield 63.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an anhydrous DCM (50 mL) solution of t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((methylamino)methyl)phenoxy)acetate (22) (28 g, 72 mmol), was added Et3N (8.6 g, 85 mmol) followed by portionwise addition of 4-fluoro-benzenesulfonyl chloride (16.6 g, 85 mmol). The mixture was stirred at room temperature for 20 min and water (20 mL) was added. The organic layer was separated, dried and concentrated in vacuo. The crude was purified by column chromatography to give t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (23) (24 g, 63%).

Workup

  1. customThe organic layer was separated
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-2c2c5a25fcc84fa0a39cc82074b81b7e
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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