Tri(butyl)vinyltin → 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-vinyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

HRID 514624Notes

Reaction equation

HRID 514624 reaction equation
Br[C:2]1[N:3]=[C:4]([N+:35]([O-:37])=[O:36])[N:5]([CH2:7][C:8]2([CH2:16][O:17][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]2)[CH:6]=1.[CH2:38](C([Sn])=C(CCCC)CCCC)[CH2:39]CC>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:17]([CH2:16][C:8]1([CH2:7][N:5]2[CH:6]=[C:2]([CH:38]=[CH2:39])[N:3]=[C:4]2[N+:35]([O-:37])=[O:36])[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)[Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 903003985-{(4-bromo-2-nitro-1H-imidazol-1-yl)methyl}-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxane

Product 1

HCID 903004335-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-vinyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxaneYield 62.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

280 mg (0.48 mmol equivalents) of 5-{(4-bromo-2-nitro-1H-imidazol-1-yl)methyl}-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxane was dissolved in 4.7 mL of dimethylformamide, 278 μL (0.95 mmol equivalents) of tributylvinyltin and 55 mg (0.05 mmol equivalents) of tetrakis(triphenylphosphine)palladium were added thereto, and the mixture was heated to 80° C. in an oil bath and then stirred for 5 hours. After completion of the reaction, the reaction liquid was concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1) to give 163 mg (0.30 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-vinyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. concentrationwas concentrated under vacuum
  4. customthe obtained crude product
  5. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1)

Sources & evidence

ORD record
ord-e14ff7b4bdce4ce3aa14aaa811fb0914
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

Loading…