2-Chloro-1-methylpyridinium iodide → HCID 59408770, compound

HRID 1188116Notes

Reaction equation

HRID 1188116 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[N:11]=[C:10]([C:19]([OH:21])=O)[CH:9]=2)=[CH:4][CH:3]=1.[I-].ClC1C=CC=C[N+:25]=1C.[Br:31][C:32]1[CH:40]=[CH:39][C:35](C(O)=O)=[CH:34][N:33]=1>C1COCC1.CCN(C(C)C)C(C)C>[Br:31][C:32]1[N:33]=[C:34]([NH:25][C:19]([C:10]2[CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:12]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[N:11]=2)=[O:21])[CH:35]=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 1670692-Chloro-1-methylpyridinium iodideHCID 2389326-Bromonicotinic acidHCID 59408741HCID 59408741, compound

Product 1

HCID 59408770HCID 59408770, compoundYield 29.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a suspension of 5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid 1 (400 mg, 1.37 mmol) and 2-chloro-1-methylpyridinium iodide (524 mg, 2.0 mmol) in THF (20 ml), DIPEA (0.46 ml) followed by 6-bromopyridin-2-amine 2 (237 mg, 1.37 mmol) were added. The suspension was stirred for 72 hrs. Then the reaction mixture was concentrated, diluted in water (10 ml) and extracted with dichloromethane (50 ml×2). All organic phases were washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified on a silica gel column (EtOAc: pet-ether 1:4) to give N-(6-bromopyridin-2-yl)-5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxamide 3 (180 mg) as a white solid. Mp. 151-152° C.

Workup

  1. additionwere added
  2. concentrationThen the reaction mixture was concentrated
  3. additiondiluted in water (10 ml)
  4. extractionextracted with dichloromethane (50 ml×2)
  5. washAll organic phases were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified on a silica gel column (EtOAc: pet-ether 1:4)

Sources & evidence

ORD record
ord-0a782c9f927c4e499200a2007d2aaae2
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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