HCID 68276009, compound → HCID 68353095, compound

HRID 1475953Notes

Reaction equation

HRID 1475953 reaction equation
[Br:1][C:2]1[C:23](C(O)=O)=[C:5]2[CH:6]=[C:7]([C:10](=[O:22])[N:11]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:8]=[CH:9][N:4]2[N:3]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:23]=[C:5]2[CH:6]=[C:7]([C:10]([N:11]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])=[O:22])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

3

Reactant 1

HCID 68276009HCID 68276009, compound

Product 1

HCID 68353095HCID 68353095, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 2-bromo-5-(diisopentylcarbamoyl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (0.285 g, 0.672 mmol) in diphenyl ether (6 ml) was heated to 210° C. for 9 hours. The mixture was allowed to cool, loaded on a silica gel pad, rinsed with diethyl ether (10 mL) and dried thoroughly under vacuum. The dried silica gel pad was then connected to a 24 g silica gel ISCO Gold cartridge and eluted with hexanes for 3 min then 0% to 100% ethyl acetate over 11 min. Concentration of the desired fractions afforded 2-bromo-N,N-diisopentylpyrazolo[1,5-a]pyridine-5-carboxamide (0.19 g, 0.475 mmol, 70.7% yield) as a yellow oil. LCMS m/z 380.1, 382.1 (M+H)+

Workup

  1. temperatureto cool
  2. washrinsed with diethyl ether (10 mL)
  3. customdried thoroughly under vacuum
  4. washeluted with hexanes for 3 min

Sources & evidence

ORD record
ord-bb4d2ec8a7634d5096a352a11ca80ba4
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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