Potassium Carbonate → HCID 86584824, compound

HRID 1835344Notes

Reaction equation

HRID 1835344 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])=[CH:12][C:13]([C:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH:21]=2)=[N:14][CH:15]=1)=[O:9].Br[CH2:40][CH:41]1[CH2:43][CH2:42]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[F:36][C:33]([F:34])([F:35])[C:31]1[CH:30]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:37])[F:38])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])=[CH:12][C:13]([C:16]2[CH2:17][CH2:18][N:19]([CH2:40][CH:41]3[CH2:43][CH2:42]3)[CH2:20][CH:21]=2)=[N:14][CH:15]=1)=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 10302116HCID 10302116, compound

Product 1

HCID 86584824HCID 86584824, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 60 mg (0.11 mmol) 4-o-tolyl-1′,2′,3′, 6′-tetrahydro-[2,4′]bipyridinyl-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide (Example 42), 0.011 ml (0.11 mmol) (bromomethyl)cyclopropane and 19 mg (0.14 mmol) potassium carbonate in 1.5 ml acetonitrile was stirred at room temperature for 15 h. The mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with three portions of ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated. Column chromatography afforded 28 mg (42%) of the title compound as a light brown solid.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with three portions of ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-34effda2eb2845fd85a54d92f3e449b1
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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