Azido(trimethyl)stannane → HCID 178517018, compound

HRID 1271407Notes

Reaction equation

HRID 1271407 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[CH2:13][CH:12]1[C:14]#[N:15].C[Sn]([N:20]=[N+:21]=[N-:22])(C)C>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[CH2:13][CH:12]1[C:14]1[NH:22][N:21]=[N:20][N:15]=1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 18453546HCID 18453546, compound

Product 1

HCID 178517018HCID 178517018, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
5 °C

Procedure

A suspension containing 5′-bromo-2-cyano-spiro[cyclopropane-1,3′-[3H]indol]-2′(1′H)-one (263 mg, 1 mmol) and trimethyltin azide(384 mg, 2 mmol) in xylene (20 mL) was stirred and heated to reflux for 16 hours. After cooling the solution to 5° C., a white precipitate was obtained that gave 210 mg (yield: 69%) of the title compound. MS: m/z 206 [M+1]+; 1H NMR (DMSO-d6): δ 10.7 (br, 1H), 7.14 (m, 1H), 7.0 (m, 2H), 6.70 (d, 1H), 2.90 (m, 1H), 2.24 (m, 1H). 1.98 (m, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. customa white precipitate was obtained

Sources & evidence

ORD record
ord-455c6d59b79245838608c899b6c2a15e
Source dataset
uspto-grants-2007_04
Patent number
US07205328B2

Reaction notes

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