Potassium Phosphate, Tribasic → N-(6-(3-tert-butyl-5-(2,4-di-tert-butoxypyrimidin-5-yl)-2-vinyl phenyl)naphthalen-2-yl)methanesulfonamide

HRID 403685Notes

Reaction equation

HRID 403685 reaction equation
[C:1]([C:5]1[C:6](I)=[C:7]([C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[CH:33]=[C:32]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:31]=[CH:30]3)[CH:8]=[C:9]([C:11]2[C:12]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:13][C:14]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:43]([Sn](CCCC)(CCCC)C=C)[CH2:44]CC.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC12CC3(C)P(C4C=CC=CC=4)C(C)(CC(C)(O3)O1)O2>CS(C)=O.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]>[C:1]([C:5]1[C:6]([CH:43]=[CH2:44])=[C:7]([C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[CH:33]=[C:32]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:31]=[CH:30]3)[CH:8]=[C:9]([C:11]2[C:12]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:13][C:14]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 81998TributylvinyltinHCID 534277901,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantaneHCID 66833989N-(6-(3-tert-butyl-5-(2,4-di-tert-butoxypyrimidin-5-yl)-2-iodo phenyl)naphthalen-2-yl)methanesulfonamide

Product 1

HCID 66834092N-(6-(3-tert-butyl-5-(2,4-di-tert-butoxypyrimidin-5-yl)-2-vinyl phenyl)naphthalen-2-yl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a 5 mL microwave tube was added the product from Example 34 Part A (210 mg, 0.3 mmol), tributyl(vinyl)stannane (0.175 mL, 0.600 mmol), potassium phosphate (134 mg, 0.63 mmol), 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (8.77 mg, 0.030 mmol) and tris(dibenzylideneacetone)dipalladium(0) (13.74 mg, 0.015 mmol) in dimethyl sulfoxide (3 mL). The mixture was purged with nitrogen for 5 minutes and microwaved at 100° C. for 1 hour. The reaction mixture was partitioned with ethyl acetate and 0.1 M HCl. The organic layer was washed with saturated NaHCO3, brine, dried (Na2SO4), filtered and the filtrate treated with 3-mercaptopropyl functionalized silica gel, filtered and concentrated in vacuo to give crude product which was purified by silica gel flash chromatography eluting with ethyl acetate/hexane (10% to 20%) to give the title compound.

Workup

  1. customThe mixture was purged with nitrogen for 5 minutes
  2. custommicrowaved at 100° C. for 1 hour
  3. customThe reaction mixture was partitioned with ethyl acetate and 0.1 M HCl
  4. washThe organic layer was washed with saturated NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. additionthe filtrate treated with 3-mercaptopropyl functionalized silica gel
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give crude product which
  11. customwas purified by silica gel flash chromatography
  12. washeluting with ethyl acetate/hexane (10% to 20%)

Sources & evidence

ORD record
ord-6305d82d475947f29c90f8f913989c8a
Source dataset
uspto-grants-2014_06
Patent number
US08748443B2

Reaction notes

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