Azido(trimethyl)stannane → HCID 22477642, compound

HRID 2182223Notes

Reaction equation

HRID 2182223 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-c115fdfe186041b481bf12d75c80dab0
Source dataset
uspto-grants-2005_05
Patent number
US06897207B2

Reaction notes

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