2-Chloropyridine → HCID 67344078, compound

HRID 1910847Notes

Reaction equation

HRID 1910847 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[S:14][CH:15]=[C:16]([NH2:18])[N:17]=3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.Cl[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.C1(P(C(C)(C)C)F)CCCCC1.CC(C)([O-])C.[Na+]>COCCOC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[S:14][CH:15]=[C:16]([NH:18][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[N:17]=3)[CH:10]=[N:9]2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 79772-ChloropyridineHCID 23676156Sodium t-butoxideHCID 58071418CyPF-tBuHCID 67345116HCID 67345116, compound

Product 1

HCID 67344078HCID 67344078, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

According to Scheme 1 Step 9: A solution of 2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-4-amine (0.70 mmol, 200 mg), 2-chloropyridine (0.70 mmol, 65.6 μL), CyPF-tBu (52 μmol, 29.4 mg), Pd(OAc)2 (52 μmol, 11.8 mg) and sodium tert-butoxide (0.98 mmol, 71.4 mg) in DME (698 μL) was stirred at 80° C. for 12 hours under nitrogen in a microwave tube. After filtration through celite, the resulting crude product was purified by flash chromatography over silica gel using DCM/EtOH/NH3 (100:0:0 to 95:4.5:0.5) as eluent to afford N-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-4-yl)pyridin-2-amine (0.39 mmol, 144 mg, 57%).

Workup

  1. filtrationAfter filtration through celite
  2. customthe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-2df94758c19043b6acb6762c75695a7b
Source dataset
uspto-grants-2013_12
Patent number
US08604033B2

Reaction notes

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