Tributylvinyltin → HCID 86669566, compound

HRID 524440Notes

Reaction equation

HRID 524440 reaction equation
Br[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:33])[CH:13]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH:30]4[CH2:32][CH2:31]4)(=[O:29])=[O:28])=[CH:23][CH:22]=3)[O:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:10][C:5]2=[CH:4][CH:3]=1.[Li+].[Cl-].[CH2:36]([Sn](CCCC)(CCCC)C=C)[CH2:37]CC>C1COCC1.CN(C=O)C.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>[CH:30]1([S:27]([C:24]2[CH:25]=[CH:26][C:21]([CH:13]([O:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:12]([NH:11][C:9]3[S:8][C:6]4[C:5]([N:10]=3)=[CH:4][CH:3]=[C:2]([CH:36]=[CH2:37])[N:7]=4)=[O:33])=[CH:22][CH:23]=2)(=[O:29])=[O:28])[CH2:32][CH2:31]1

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 56591642HCID 56591642, compound

Product 1

HCID 86669566HCID 86669566, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To mixture of N-(5-Bromo-thiazolo[5,4-b]pyridin-2-yl)-2-(4-cyclopropanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yloxy)-acetamide (Example-A95) (0.135 g, 0.24 mmol), Pd(PPh3)4 (0.014 g, 0.012 mmol) and LiCl (0.031 g, 0.73 mmol) in THF:DMF (1:1, 5 mL) under inert atmosphere was added tributyl(vinyl)stannane (0.23 g, 0.73 mmol) and heated under reflux for 8 hrs. Solvent was removed in vacuo and taken into brine and extracted with ethyl acetate (3×5 mL), washed with water and brine, dried (Na2SO4) and concentrated in vacuo to afford titled compound (0.080 g)

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 hrs
  3. customSolvent was removed in vacuo
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5b8f6b7ae814f299363cd5335864ac0
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

Loading…