Triethylamine → HCID 86654639, compound

HRID 1426184Notes

Reaction equation

HRID 1426184 reaction equation
[N:1]1[N:5]2[CH:6]=[C:7](O)[CH:8]=[CH:9][C:4]2=[CH:3][CH:2]=1.[O-]S(C(F)(F)F)(=O)=O.[CH2:19](N(CC)CC)[CH3:20]>ClCCl>[C:19]([C:7]1[CH:8]=[CH:9][C:4]2[N:5]([N:1]=[CH:2][CH:3]=2)[CH:6]=1)#[CH:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2758875TrifluoromethanesulfonateHCID 15257897HCID 15257897, compound

Product 1

HCID 86654639HCID 86654639, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 6-ethynyl-pyrazolo[1,5-a]pyridine of formula ID can be obtained by decarboxylation of an appropriately substituted 6-methoxy-pyrazolo[1,5-a]pyridine-3-carboxylic acid ester 22 with hydrobromic acid, yielding the corresponding pyrazolo[1,5-a]pyridin-6-ol derivative 23, which is converted to the triflate derivative 25 using trifluoromethanesulfonic anhydride 24 and a base such as triethylamine in a solvent such as dichloromethane. Sonogashira coupling of 25 with an aryl-acetylene of formula 3 yields the desired 6-ethynyl-pyrazolo[1,5-a]pyridine of formula ID (scheme 5).

Sources & evidence

ORD record
ord-96019268dc044e65a752267f91132ae8
Source dataset
uspto-grants-2015_01
Patent number
US08933094B2

Reaction notes

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