Azido(trimethyl)stannane → HCID 22477642, compound

HRID 1765597Notes

Reaction equation

HRID 1765597 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[C:4]([C:13]2[N:21]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=2)=[CH:3]1.[CH3:32][Sn:33]([N:36]=[N+:37]=[N-:38])([CH3:35])[CH3:34]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[N:36]([Sn:33]([CH3:35])([CH3:34])[CH3:32])[N:37]=[N:38][N:12]=3)=[CH:8][CH:9]=2)[C:4]([C:13]2[N:21]([S:22]([C:25]3[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=3)(=[O:23])=[O:24])[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 22477547HCID 22477547, compound

Product 1

HCID 22477642HCID 22477642, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indole-5-carbonitrile [100 mg, Reference Example 13(c)] in toluene (10 mL) was treated with trimethyltin azide (56 mg, 0.28 mmol) then heated under reflux for 14 hours. The white precipitate was collected by filtration washed with toluene (10 mL) and then dried to give the title compound (125 mg) as a colourless solid, m.p. 240–243° C. (with decomposition). MS: 633(MH+).

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 14 hours
  3. filtrationThe white precipitate was collected by filtration
  4. washwashed with toluene (10 mL)
  5. customdried

Sources & evidence

ORD record
ord-cac21447559b4e77a5d657375743643f
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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