Diisopropylethylamine → HCID 59408770, compound

HRID 1188119Notes

Reaction equation

HRID 1188119 reaction equation
[I-].ClC1C=CC=C[N+:4]=1C.CCN(C(C)C)C(C)C.[Br:19][C:20]1[CH:28]=[CH:27][C:23](C(O)=O)=[CH:22][N:21]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[N:40]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][O:42]3)[N:39]=[C:38]([C:47]([OH:49])=O)[CH:37]=2)=[CH:32][CH:31]=1>C(Cl)Cl.CN(C=O)C>[Br:19][C:20]1[N:21]=[C:22]([NH:4][C:47]([C:38]2[CH:37]=[C:36]([C:33]3[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=3)[N:40]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][O:42]3)[N:39]=2)=[O:49])[CH:23]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 2389326-Bromonicotinic acidHCID 59408741HCID 59408741, compound

Product 1

HCID 59408770HCID 59408770, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

2-Chloro-1-methylpyridinium iodide (950 mg, 3.7 mmol) and DIPEA (0.7 mL) were added to a solution of 6-bromopicolinic acid 2 (500 mg, 2.47 mmol) in dry DCM/DMF (30/5 mL). The reaction mixture was stirred for 1 hr. tert-Butyl 3-amino-5-(4-fluorophenyl)-1H-pyrazole-1-carboxylate 1 was added (650 mg, 2.47 mmol). The resulting yellow reaction mixture was stirred for 3 days. Then the reaction mixture was concentrated under reduced pressure, the residue was diluted in chloroform and washed with water and brine, and then dried over Na2SO4. The resulting crude mixture was purified on silica gel (EtOAc: pet-ether, 1:3) to give 6-bromo-N-(5-(4-fluorophenyl)-1H-pyrazol-3-yl) picolinamide 3 (450 mg, 50%) as a white solid.

Workup

  1. stirringThe resulting yellow reaction mixture was stirred for 3 days
  2. concentrationThen the reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted in chloroform
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. customThe resulting crude mixture was purified on silica gel (EtOAc: pet-ether, 1:3)

Sources & evidence

ORD record
ord-c02a86ff7d4543bbbaac33a7127c3d01
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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