tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate → HCID 136063646, compound

HRID 2382796Notes

Reaction equation

HRID 2382796 reaction equation
Br[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C(OC([N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1)=O)(C)(C)C>>[NH:27]1[CH:31]=[C:30]([C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH:29]=[N:28]1

Participants

3

Reactant 2

HCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 25212513N-(5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamide

Product 1

HCID 136063646HCID 136063646, compoundYield 32%

Procedure

The title compound was prepared following procedure described for intermediate A1 step a), but starting from N-(5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamide ((B1), 75 mg; 0.24 mmol; 1.0 eq.) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester (139 mg; 0.47 mmol; 2.0 eq.), at 140° C. for 14 h. Further treatment with a 1 N methanolic HCl solution (0.5 mL) and purification by flash chromatography on silica (EtOAc/c-Hex, 80:20) gave the title compound as a white powder (23 mg, 32%). HPLC, Rt: 2.07 min. (purity 96.9%). LC/MS, M+(ESI): 305.3, M−(ESI): 303.3.

Workup

  1. customThe title compound was prepared following procedure
  2. customFurther treatment with a 1 N methanolic HCl solution (0.5 mL) and purification by flash chromatography on silica (EtOAc/c-Hex, 80:20)

Sources & evidence

ORD record
ord-032ac53e65d74ebeb04120de68a5106d
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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