2,6-Lutidine → HCID 66868198, compound

HRID 68586Notes

Reaction equation

HRID 68586 reaction equation
[Br:1][C:2]1[CH:16]=[C:15]([CH2:17][NH:18][CH3:19])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].CC1C=CC=C(C)N=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>C(Cl)Cl>[Br:1][C:2]1[CH:16]=[C:15]([CH2:17][N:18]([CH3:19])[S:35]([C:32]2[CH:33]=[CH:34][C:29]([F:28])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 66868764t-Butyl 2-(2-bromo-4-((methylamino)methyl)phenoxy)acetate

Product 1

HCID 66868198HCID 66868198, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl 2-(2-bromo-4-((methylamino)methyl)phenoxy)acetate (2) (4.4 g, 13.4 mmol, 1 eq) in DCM (50 mL) was added 2,6-lutidene (3.1 ml, 26.8 mmol, 2 eq) and 4-fluorobenzenesulfonyl chloride (2.9 g, 14.7 mmol. 1.1 eq, Aldrich, Milwaukee, Wis., USA). After the mixture was stirred for 18 h at room temperature, it was washed with 1 N HCl (100 mL), saturated NaHCO3 (100 mL), and brine (100 mL). The washed DCM layer was dried over Na2SO4 and concentrated in vacuo. Silica gel purification (linear gradient of 0% EtOAc/hexanes to 100% EtOAc/hexanes) of the resultant residue yielded 2.95 g (44.8%) of t-butyl 2-(2-bromo-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (3) as a white solid. 1HNMR (CDCl3, 300 MHz): δ 7.82 (m, 2H), 7.44 (d, 1H), 7.22 (m, 3H), 6.72 (d, 1H), 4.57 (s, 2H), 4.04 (s, 2H), 2.58 (s, 3H), 1.46 (s, 9H).

Workup

  1. washit was washed with 1 N HCl (100 mL), saturated NaHCO3 (100 mL), and brine (100 mL)
  2. dry with materialThe washed DCM layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customSilica gel purification (linear gradient of 0% EtOAc/hexanes to 100% EtOAc/hexanes) of the resultant residue

Sources & evidence

ORD record
ord-8ddf648422074e94b58d6a2dd30229ed
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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