Triethylamine → 2,2,2-trifluoro-N-{4-[(6-methoxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}ethanesulfonamide

HRID 1993006Notes

Reaction equation

HRID 1993006 reaction equation
[CH3:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([O:14][C:15]2[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.CCN(CC)CC.[F:35][C:36]([F:43])([F:42])[CH2:37][S:38](Cl)(=[O:40])=[O:39]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:35][C:36]([F:43])([F:42])[CH2:37][S:38]([NH:19][C:18]1[CH:20]=[CH:21][C:15]([O:14][C:4]2[C:5]3[C:10](=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=3)[CH:11]=[C:2]([CH3:1])[C:3]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][CH:17]=1)(=[O:40])=[O:39]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 685373984-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}aniline

Product 1

HCID 685377272,2,2-trifluoro-N-{4-[(6-methoxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}ethanesulfonamideYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A flask containing a solution of 29 (0.30 g, 0.85 mmol), Et3N (0.26 g, 2.55 mmol) and DMAP (0.032 g, 0.26 mmol) in CH2Cl2 (5 mL) was added trifluoroethanesulfonyl chloride (0.39 g, 2.13 mmol), dropwise, at RT and the reaction allowed to stir overnight at RT. After 18 h the reaction was diluted with 15 mL CH2Cl2 and rinsed with 10% aq. HCl (25 mL). The CH2CO2 layer was dried (MgSO4), concentrated to a dark amber oil, and purified by silica gel column chromatography with 10% EtOAc/hexanes to afford 270 mg (64%) of the title compound, 273, as a white foam. 1H NMR (400 MHz, DMSO-d6): δ 2.18 (s, 3H), 3.88 (s, 3H), 4.33 (q, J=9.8 Hz, 2H), 6.58 (d, J=9.0 Hz, 2H), 6.98 (d, J=9.0 Hz, 2H), 7.08 (dd, J1=2.4 Hz, J2=9.1 Hz, 1H), 7.18-7.36 (m, 5H), 7.61 (d, J=9.1 Hz, 1H), 7.70 (s, 1H), 10.07 (s, 1H).

Workup

  1. customat RT
  2. washrinsed with 10% aq. HCl (25 mL)
  3. dry with materialThe CH2CO2 layer was dried (MgSO4)
  4. concentrationconcentrated to a dark amber oil
  5. custompurified by silica gel column chromatography with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-dee8e3587f5f48a5b7d59e0d343b6370
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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