Azido(trimethyl)stannane → HCID 178492771, compound

HRID 2221651Notes

Reaction equation

HRID 2221651 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[C:23]([CH2:25][O:26][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[CH:22]=[CH:21][C:4]=1[O:5][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[O:10][C:11]=1[CH3:12].C[Sn]([N:41]=[N+:42]=[N-:43])(C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:24]=[C:23]([CH2:25][O:26][Si:27]([CH:28]([CH3:29])[CH3:30])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[CH:22]=[CH:21][C:4]=1[O:5][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:14]=[C:15]([C:16]3[NH:43][N:42]=[N:41][N:17]=3)[CH:18]=[CH:19][CH:20]=2)[O:10][C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 69216103HCID 69216103, compound

Product 1

HCID 178492771HCID 178492771, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-{4-[(2-methoxy-4-{[(triisopropylsilyl)oxy]methyl}phenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzonitrile (0.52 g), trimethyl tin azide (0.62 g) and toluene (10 mL) was heated under reflux for 15 hrs. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography to give 5-(3-{4-[(2-methoxy-4-{[(triisopropylsilyl)oxy]methyl}phenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl)-1H-tetrazole as colorless crystals (0.36 g, yield 65%), from a fraction eluted with ethyl acetate-methanol (95:5, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 152-153° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hrs
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-52fa5d2aceb946bbb649da862877ef88
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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