Potassium Carbonate → HCID 67954030, compound

HRID 1916855Notes

Reaction equation

HRID 1916855 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:25])=[C:9]([NH:11][S:12]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[N:10]=2)[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[F:32][C:33]([F:44])([F:43])[O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=1>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:25])=[C:9]([N:11]([CH2:39][C:38]3[CH:41]=[CH:42][C:35]([O:34][C:33]([F:32])([F:43])[F:44])=[CH:36][CH:37]=3)[S:12]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 67953927HCID 67953927, compound

Product 1

HCID 67954030HCID 67954030, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of compound 6-E (0.300 g, 0.75 mmol) and K2CO3 (0.218 g, 1.58 mmol) in DMF (5 mL) was cooled in an ice bath and treated with a solution of 4-trifluoromethoxybenzyl bromide (0.132 mL, 0.83 mmol) in DMF (1 mL) and stirred at ambient temperature for 18 hours. The solution was partitioned between EtOAc and water, and the organic phase was separated, washed with water (3×) then brine and dried over sodium sulfate. The solvent was evaporated in vacuo, and the residue was pre-absorbed on silica gel and purified by flash chromatography, using a gradient of EtOAc (10-50%) in heptanes as the eluant, to give the Compound 118, as a colorless solid (0.330 g, 82%). 1H-NMR (CDCl3): δ 8.17 (d, J=8.6 Hz, 2H), 7.85 (d, J=8.6 Hz, 8H), 7.69-7.74 (m, 1H), 7.41 (dd, J=9.9, 5.0 Hz, 1H), 7.29 (d, J=8.6 Hz, 2H), 7.03-7.14 (m, 3H), 4.74 (s, 2H), 3.97 (s, 3H), 2.26 (s, 3H); MS: m/z 538.0 (MH+).

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe solution was partitioned between EtOAc and water
  3. customthe organic phase was separated
  4. washwashed with water (3×)
  5. dry with materialbrine and dried over sodium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was pre-absorbed on silica gel
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-69cc6061df9e4fd5b7a0e1b6af6b4ba2
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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