Water → HCID 59599434, compound

HRID 1627554Notes

Reaction equation

HRID 1627554 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]([N:33](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[C:19]([O:21][CH:22]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[C:26]([F:31])[C:25]=3[Cl:32])[CH3:23])[CH:20]=2)=[CH:11][CH:10]=1.O.C(=O)(O)[O-].[Na+]>ClCCl>[Br:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]([NH2:33])=[C:19]([O:21][CH:22]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[C:26]([F:31])[C:25]=3[Cl:32])[CH3:23])[CH:20]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59599410HCID 59599410, compound

Product 1

HCID 59599434HCID 59599434, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of 6′-bromo-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-[3,3′]bipyridinyl-6-yl-bis-(tert-butoxycarbonyl)-amine (1.3 g, 2.0 mmol) in dichloromethane (15 mL). After 3 hours, equal portions of water and saturated aqueous sodium bicarbonate were added. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over Na2SO4 and concentrated by rotary evaporation to give 6′-bromo-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-[3,3′]bipyridinyl-6-ylamine (968 mg, 106%).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-e170948bcbf347b5a82b038dda2addda
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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