Tributylvinyltin → HCID 19605526, compound

HRID 1603565Notes

Reaction equation

HRID 1603565 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[N:3]=1.[CH:23]([Sn](CCCC)(CCCC)CCCC)=[CH2:24]>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].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>[N:18]1([C:4]2[CH:5]=[C:6]([S:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)(=[O:10])=[O:9])[CH:7]=[C:2]([CH:23]=[CH2:24])[N:3]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 69186894-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine

Product 1

HCID 19605526HCID 19605526, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

0.38 g (0.001 Mol) 4-(2-Bromo-6-pyrrolidin-1-yl-pyridine-4-sulfonyl)-phenylamine, 0.116 g (0.0001 Mol) Pd(PPh3)4 and 0.292 ml (0.001 Mol) vinyl-tributylstannane were stirred at reflux for 18 h in a mixture of dioxane (10 ml) and 2N Na2CO3 (2 ml). Then the solvent was evaporated, the residue was taken up in ethyl acetate, washed with water and brine and dried over Na2SO4. After chromatography on SiO2 with ethyl acetate hexane 2:3 the product containing fractions were evaporated and the residue taken up in hexane. The suspension was stirred for 1 h and then filtered. The residue on the filter was washed with hexane (10 ml) and dried in a high vacuum. It was obtained 0.16 g (49%) 4-(2-pyrrolidin-1-yl-6-vinyl -pyridine-4-sulfonyl)-phenylamine as a yellow solid; mp.: 181-182° C.

Workup

  1. customThen the solvent was evaporated
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. additionAfter chromatography on SiO2 with ethyl acetate hexane 2:3 the product containing fractions
  5. customwere evaporated
  6. filtrationfiltered
  7. washThe residue on the filter was washed with hexane (10 ml)
  8. customdried in a high vacuum

Sources & evidence

ORD record
ord-b05a4edcfa4c4679a622f61c0d4f1954
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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