N-(6-(3-tert-butyl-5-(2,4-di-tert-butoxypyrimidin-5-yl)-2-vinyl phenyl)naphthalen-2-yl)methanesulfonamide → N-(6-(3-tert-butyl-5-(2,4-di-tert-butoxypyrimidin-5-yl)-2-ethyl phenyl)naphthalen-2-yl)methanesulfonamide
Reaction equation
[C:1]([C:5]1[C:6]([CH:42]=[CH2:43])=[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]>[Pd].CO>[C:1]([C:5]1[C:6]([CH2:42][CH3:43])=[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]([CH3:19])([CH3:20])[CH3:21])=[N:15][CH:16]=2)[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a 100 mL round-bottomed flask was added the product from Example 35 Part A (132 mg, 0.219 mmol), 10% palladium on carbon (20 mg, 0.019 mmol) and methanol (10 mL). The mixture was hydrogenated for 24 hours, 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
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give crude product which
- customwas purified by silica gel flash chromatography
- washeluting with ethyl acetate/hexane (10% to 20%)
Sources & evidence
- ORD record
- ord-30640405244341248d133209cbafb72a
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353091B2
Reaction notes
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