Tributyltin azide → Ethyl 5-(1H-tetrazol-5-ylmethyl)imidazo[1,2-a]pyridine-2-carboxylate

HRID 862002Notes

Reaction equation

HRID 862002 reaction equation
[C:1]([CH2:3][C:4]1[N:9]2[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1)#[N:2].[N:18]([Sn](CCCC)(CCCC)CCCC)=[N+:19]=[N-:20]>P(CC1C2N(C=C(C(O)=O)N=2)C=CC=1)(O)(O)=O>[NH:18]1[C:1]([CH2:3][C:4]2[N:9]3[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=[C:8]3[CH:7]=[CH:6][CH:5]=2)=[N:2][N:20]=[N:19]1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 19701198Ethyl 5-(cyanomethyl)imidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 178469441Ethyl 5-(1H-tetrazol-5-ylmethyl)imidazo[1,2-a]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 19701381HCID 19701381, compoundSolvent2×

Procedure

The title material is prepared by heating the title product of Example 99 with azido tributylstannane at 80° C. for 72 h. After cooling to room temperature, the reaction is treated with methanolic HCl for 30 min., diluted with 4N HCl, washed with diethyl ether and concentrated to yield title material.

Workup

  1. washwashed with diethyl ether
  2. concentrationconcentrated
  3. customto yield title material

Sources & evidence

ORD record
ord-1add0950defb45b38b2876b3671ad414
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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