HCID 118324115, compound → HCID 118324071, compound

HRID 1778251Notes

Reaction equation

HRID 1778251 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8](=[O:13])N(OC)C)[CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([Mg]Br)=[CH:25][CH:24]=1>O1CCCC1.[Cl-].[Na+]>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)=[O:13])[CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 118324115HCID 118324115, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 118324071HCID 118324071, compound

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 1-L round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl N-[2-bromo-4-[methoxy(methyl)carbamoyl]phenyl]carbamate (30 g, 83.52 mmol, 1.00 equip) in tetrahydrofuran (400 mL). To the resulting mixture was then added (4-chlorophenyl)magnesium bromide (250 mL, 3.00 equip, 1 M) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with saturated sodium chloride (200 mL). The resulting solution was extracted with ethyl acetate (400 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The resulting residue was recrystallized from ethyl acetate:petroleum ether in a ratio of 1:20. The solids were collected by filtration. The mother liquor was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10) to yield additional tert-butyl N-[2-bromo-4-[(4-chlorophenyl)carbonyl]phenyl]carbamate as a light yellow solid. LCMS (ES, m/z) 410 [M+H]+

Workup

  1. customInto a 1-L round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. extractionThe resulting solution was extracted with ethyl acetate (400 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered out
  6. concentrationThe resulting mixture was concentrated under vacuum
  7. customThe resulting residue was recrystallized from ethyl acetate
  8. filtrationThe solids were collected by filtration
  9. concentrationThe mother liquor was concentrated under vacuum

Sources & evidence

ORD record
ord-64115aaaa1944133918830339453403f
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

Loading…