Tri(butyl)vinyltin → HCID 54535880, compound

HRID 2301040Notes

Reaction equation

HRID 2301040 reaction equation
[CH2:1](C([Sn])=C(CCCC)CCCC)[CH2:2]CC.Br[C:17]1[CH:22]=[C:21]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:20]=[CH:19][C:18]=1[NH:36][C:37](=[O:45])[C@:38]([OH:44])([CH3:43])[C:39]([F:42])([F:41])[F:40]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:1]([C:17]1[CH:22]=[C:21]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:20]=[CH:19][C:18]=1[NH:36][C:37](=[O:45])[C@:38]([OH:44])([CH3:43])[C:39]([F:42])([F:41])[F:40])=[CH2:2]

Participants

5

Reactant 2

HCID 53438229Tri(butyl)vinyltin2×HCID 54101286HCID 54101286, compound

Product 1

HCID 54535880HCID 54535880, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 1140TolueneSolvent

Procedure

Tributylvinyltin (0.28 ml) was added to a deoxygenated suspension of (R)-N-[2-bromo-4-(4-mesylphenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 140) (0.50 g) and tris(dibenzylideneacetone)dipalladium(0) (0.05 g) in anhydrous toluene (10 ml). The mixture was heated under reflux with stirring. After 14 hours a further portion of tris(dibenzylideneacetone)dipalladium(0) (0.05 g) and tributylvinyltin (0.28 ml) was added and heating was continued for a further 7 hours. The reaction mixture was allowed to cool and volatile materials were removed by evaporation. The residue was purified on a silica gel Mega Bond Elut column eluting with 5-50% ethyl acetate/hexane to give the title compound (0.146 g) as a solid. NMR (CDCl3) 1.74 (s, 3H), 3.06 (s, 3H), 5.65-5.82 (dd, 2H), 6.67-6.77 (dd, 1H), 7.86-7.89 (dd, 1H), 7.95 (s, 1H), 8.06-8.16 (m, 4H), 8.35 (d, 1H), 8.79 (s, 1H); MS (ESP−): 477.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. temperatureheating
  4. temperatureto cool
  5. customvolatile materials were removed by evaporation
  6. customThe residue was purified on a silica gel Mega Bond Elut column
  7. washeluting with 5-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-fd857f975fa24b05b9846ee14ff3f782
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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