Hydrogen Bromide → N-(3-bromomethyl-4-{(E)-2-[3-tert-butyl-2-methoxy-5-(6-methoxy-2-oxo-1,2-dihydro-pyridin-3-yl)-phenyl]-vinyl}-phenyl)-methanesulfonamide

HRID 2390857Notes

Reaction equation

HRID 2390857 reaction equation
[C:1]([C:5]1[C:6]([O:37][CH3:38])=[C:7](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][C:26]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:25][C:24]=2[CH2:34]OC)[CH:8]=[C:9]([C:11]2[C:12]([O:19]C)=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[BrH:39].C([O-])(O)=O.[Na+]>CC(O)=O>[Br:39][CH2:34][C:24]1[CH:25]=[C:26]([NH:29][S:30]([CH3:33])(=[O:31])=[O:32])[CH:27]=[CH:28][C:23]=1/[CH:22]=[CH:21]/[C:7]1[CH:8]=[C:9]([C:11]2[C:12](=[O:19])[NH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]=1[O:37][CH3:38]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 68537390N-(4-{(E)-2-[3-tert-butyl-5-(2,6-dimethoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-3-methoxymethyl-phenyl) methanesulfonamide

Product 1

HCID 68540957N-(3-bromomethyl-4-{(E)-2-[3-tert-butyl-2-methoxy-5-(6-methoxy-2-oxo-1,2-dihydro-pyridin-3-yl)-phenyl]-vinyl}-phenyl)-methanesulfonamideYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

step 2—A solution of 322 (104 mg, 0.193 mmol), HBr 48% (0.100 mL, 0.871 mmol) in HOAc (4 mL) was heated at 75° C. for 4 h in a sealed tube. The reaction mixture was carefully poured into a mixture of saturated NaHCO3 and ice, extracted with EtOAc, dried (Na2SO4), filtered and concentrated to afford 93 mg (84%) of N-(3-bromomethyl-4-{(E)-2-[3-tert-butyl-2-methoxy-5-(6-methoxy-2-oxo-1,2-dihydro-pyridin-3-yl)-phenyl]-vinyl}-phenyl)-methanesulfonamide (324) as a purple oil.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a4209f4fa80f46388b10208c438f985d
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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