Benzyl Bromide → HCID 21865180, compound

HRID 2055979Notes

Reaction equation

HRID 2055979 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[CH:16][N:15]=[C:14]([O:18][C:19]2[C:24]3[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=3[CH:22]=[CH:21][CH:20]=2)[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CC(C)=O>[CH2:38]([O:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[CH:16][N:15]=[C:14]([O:18][C:19]2[C:24]3[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=3[CH:22]=[CH:21][CH:20]=2)[CH:13]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 135729082HCID 135729082, compound

Product 1

HCID 21865180HCID 21865180, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of N-{4-[6-(2-hydroxy-4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide, (Example 137), (0.20 g, 0.50 mmol) and potassium carbonate (0.062 g, 0.45 mmol, Aldrich) in anhydrous acetone (2 mL) was added benzyl bromide (0.053 mL, 0.45 mmol, Aldrich) and the reaction mixture was heated at 70° C. for 2 h. The solvent was removed under vacuum and the residue was diluted with water (50 mL) and extracted with ether (2×100 mL). The combined organic extracts were washed with water (100 mL), dried over Na2SO4, filtered and concentrated under vacuum. The crude material was purified by silica gel chromatography (gradient: 5-60% EtOAc/hexanes) to obtain the title compound (0.030 g, 13%) as a white solid. Mp: 201-203° C. MS (ESI, pos. ion.) m/z: 537 (M+1).

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe residue was diluted with water (50 mL)
  3. extractionextracted with ether (2×100 mL)
  4. washThe combined organic extracts were washed with water (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe crude material was purified by silica gel chromatography (gradient: 5-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8188d5a01bd74180b829879ce7f06703
Source dataset
uspto-grants-2008_02
Patent number
US07332511B2

Reaction notes

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