Azido(trimethyl)stannane → HCID 178437424, compound

HRID 1886461Notes

Reaction equation

HRID 1886461 reaction equation
[C:1]([C:3]1[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=1[C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][N:17]3[C:21]4=[N:22][C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]4[N:19]=[C:18]3[CH2:28][CH3:29])=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)=[O:6])#[N:2].C[Sn]([N:38]=[N+:39]=[N-:40])(C)C>C1(C)C=CC=CC=1>[NH:38]1[C:1]([C:3]2[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=2[C:5]([N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH2:16][N:17]4[C:21]5=[N:22][C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]5[N:19]=[C:18]4[CH2:28][CH3:29])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[O:6])=[N:2][N:40]=[N:39]1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 100258733-[N-(2-cyanobenzoyl)-5-indolyl]methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 178437424HCID 178437424, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the product of Example 8, Step B (75 mg, 0.17 mmol) in 5 mL of toluene was added trimethyltin azide (43 mg, 0.21 mmol, 1.2 eq). The mixture was heated at reflux for 18 hours. Toluene was removed in vacuo and the resultant oil was dissolved in 5 mL of THF and treated with 0.5 mL of 2.5N HCl at 0° C. for 5 minutes. The volatiles were removed in vacuo and the resultant oil was flash chromatographed with 20% of 10/1 methanol/NH4OH mixture in chloroform to yield the titled compound (48.2 mg, 60%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours
  3. customToluene was removed in vacuo
  4. dissolutionthe resultant oil was dissolved in 5 mL of THF
  5. additiontreated with 0.5 mL of 2.5N HCl at 0° C. for 5 minutes
  6. customThe volatiles were removed in vacuo
  7. customchromatographed with 20% of 10/1 methanol/NH4OH mixture in chloroform

Sources & evidence

ORD record
ord-f1d62f1ae81a4330ae89a4f8db4cd373
Source dataset
uspto-grants-1992_09
Patent number
US05151435

Reaction notes

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