Azido(trimethyl)stannane → HCID 178439910, compound

HRID 653648Notes

Reaction equation

HRID 653648 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[C:22]([C:27]#[N:28])=[N:23][CH:24]=[CH:25][CH:26]=4)=[CH:17][CH:16]=3)[C:9]([CH2:11][CH2:12][CH3:13])=[N:10][C:3]=12.C[Sn]([N:33]=[N+:34]=[N-:35])(C)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[C:22]([C:27]5[NH:35][N:34]=[N:33][N:28]=5)=[N:23][CH:24]=[CH:25][CH:26]=4)=[CH:17][CH:16]=3)[C:9]([CH2:11][CH2:12][CH3:13])=[N:10][C:3]=12

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 19889378HCID 19889378, compound

Product 1

HCID 178439910HCID 178439910, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 7-methyl-2-propyl-3-[[4-(2-cyanopyridin-3-yl)phenyl]methyl]imidazo[4,5-b]pyridine (300 mg, 0.817 mmol) and trimethylstannylazide (504mg, 2.45 mmol) in toluene (3 mL) was heated to reflux for 36 h. The mixture was cooled to rt, concentrated, then purified by flash chromatography on SiO2 (80/20/1 CH2Cl2 /MeOH/NH4OH) to give 7-methyl-2-propyl-3-[[4-[2-(1H-tetrazol-5-yl)-3-pyridinyl]phenyl]methyl]imidazo [4,5-b]pyridine as a white solid.

Workup

  1. temperatureto reflux for 36 h
  2. concentrationconcentrated
  3. custompurified by flash chromatography on SiO2 (80/20/1 CH2Cl2 /MeOH/NH4OH)

Sources & evidence

ORD record
ord-3990438e95f64d23bb203057f647ad22
Source dataset
uspto-grants-1992_07
Patent number
US05128327

Reaction notes

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