2,6-Lutidine → HCID 22481033, compound

HRID 412682Notes

Reaction equation

HRID 412682 reaction equation
[CH:1]1([C:6]2[C:15]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[O:17])=[C:14]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=3)[C:13]3[CH:12]([OH:36])[CH2:11][C:10]([CH3:38])([CH3:37])[CH2:9][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:53]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54])(=O)=O>C1(C)C=CC=CC=1>[Si:53]([O:36][CH:12]1[CH2:11][C:10]([CH3:38])([CH3:37])[CH2:9][C:8]2[N:7]=[C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:15]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:20][CH:19]=3)=[O:17])=[C:14]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=3)[C:13]1=2)([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 22481037HCID 22481037, compound

Product 1

HCID 22481033HCID 22481033, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
20 °C

Procedure

0.529 g (1 mmol) of [2-cyclopentyl-4-(3,4-difluorophenyl)-5-hydroxy-7,7-dimethyl-5,6,7,8-tetrahydro-quinolin-3-yl]-(4-trifluoromethylphenyl)-methanone are dissolved in 6 ml of abs. toluene and admixed with 0.465 ml of lutidine at −5° C. At from −5° C. to −10° C., 0.459 ml (2 mmol) of tert-butyl-dimethylsilyl trifluoromethanesulphonate is added. The mixture is stirred at 20° C. for 3 hours. The mixture is diluted with toluene, the reaction is quenched with 10% strength aqueous ammonium chloride solution and the organic phase is washed with 0.1 N hydrochloric acid and saturated aqueous sodium bicarbonate solution and dried. The solvent is distilled off under reduced pressure and the residue is then purified using a column. This gives 620 mg of colourless crystals of melting point: 128° C. -129° C.

Workup

  1. customthe reaction is quenched with 10% strength aqueous ammonium chloride solution
  2. washthe organic phase is washed with 0.1 N hydrochloric acid and saturated aqueous sodium bicarbonate solution
  3. customdried
  4. distillationThe solvent is distilled off under reduced pressure
  5. customthe residue is then purified

Sources & evidence

ORD record
ord-4eef68404a5d426ca433bf026975ab8e
Source dataset
uspto-grants-2003_05
Patent number
US06562976B2

Reaction notes

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