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

HRID 1993007Notes

Reaction equation

HRID 1993007 reaction equation
[F:1][C:2]([F:35])([F:34])[CH2:3][S:4]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25]C)=[CH:22][CH:23]=3)[CH:18]=[C:17]([CH3:27])[C:16]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:10][CH:9]=1)(=[O:6])=[O:5].B(Br)(Br)Br.CCOC(C)=O>C(Cl)Cl>[F:35][C:2]([F:1])([F:34])[CH2:3][S:4]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=3)[CH:18]=[C:17]([CH3:27])[C:16]=2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:10][CH:9]=1)(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 685377272,2,2-trifluoro-N-{4-[(6-methoxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}ethanesulfonamide

Product 1

HCID 115476242,2,2-trifluoro-N-{4-[(6-hydroxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 273 (0.14 g, 0.31 mmol) in CH2Cl2 (6 mL), chilled to −20° C. under N2, was added BBr3 (0.24 g, 0.94 mmol) dropwise, via syringe, over 1 minute. After 90 min at −20° C. the r×n was poured over 50 g ice followed by EtOAc (50 mL). The EtOAC layer was washed with brine (50 mL), dried (Na2SO4) and concentrated to a viscous yellow oil that was purified by column chromatography using a gradient of 100% CH2Cl2 to 1% MeOH: CH2Cl2 to yield a foam. The foam was crystallized from EtOAc/hexanes to yield the title compound 274, as a light yellow solid (72 mg, 55%). 1H NMR (400 MHz, DMSO-d6): δ 2.13 (s, 3H), 4.33 (q, J=9.8 Hz, 2H), 6.57 (d, J=9.0 Hz, 2H), 6.96 (d, J=9.0 Hz, 2H), 6.97 (dd, J1=2.4 Hz, J2=9.1 Hz, 1H), 7.12-7.30 (m, 5H), 7.53 (s, 1H), 7.55 (d, J=9.8 Hz, 1H), 9.40 (s, 1H), 9.84 (s, 1H), 10.06 (s, 1H).

Workup

  1. washThe EtOAC layer was washed with brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to a viscous yellow oil that
  4. customwas purified by column chromatography
  5. customCH2Cl2 to yield a foam
  6. customThe foam was crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-6c3717608d6d4d40ba9686b94da2910d
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…