3,5-Difluorobenzyl bromide → HCID 10274932, compound

HRID 2184416Notes

Reaction equation

HRID 2184416 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5]Br.[OH:11][C:12]1([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20]>>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][O:31][C:28]2[CH:27]=[CH:26][C:25]([C:12]3([OH:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]3[NH:18][S:19]([CH:22]([CH3:23])[CH3:24])(=[O:21])=[O:20])=[CH:30][CH:29]=2)[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

3

Reactant 2

HCID 5188963,5-Difluorobenzyl bromideHCID 10267727HCID 10267727, compound

Product 1

HCID 10274932HCID 10274932, compoundYield 85%

Procedure

The title compound is prepared in a manner analogous to the procedure set forth in Example 48 from 3,5-difluorobenzyl bromide and [2-hydroxy-2-(4-hydroxyphenyl)cyclohexyl][(methylethyl)sulfonyl]amine to provide 511 mg as a brown oil. This material was purified via silica gel chromatography employing the Chromatotron® using a 4000 micron rotor while eluting with a solvent of methylene chloride/ethyl acetate 4:1 to yield the title compound (360 mg, 85%) as a white solid. Ion spray M.S. 438.3 (M*−1). Calculated for C22H27NO4SF2: Theory: C 60.12, H 6.19, N 3.19. Found: C 59.32, H 6.14, N 3.26.

Workup

  1. customThe title compound is prepared in a manner analogous to the procedure
  2. customto provide 511 mg as a brown oil
  3. customThis material was purified via silica gel chromatography
  4. washwhile eluting with a solvent of methylene chloride/ethyl acetate 4:1

Sources & evidence

ORD record
ord-7d846c00df79496e80c12b08872d4236
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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