N-bromobutanimide → tert-Butyl (S)-(1-(5-amino-3,6-dibromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

HRID 2170383Notes

Reaction equation

HRID 2170383 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([Br:26])[C:5]([C@@H:8]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)=[N:6][CH:7]=1.[Br:27]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[CH:3]=[C:4]([Br:26])[C:5]([C@@H:8]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)=[N:6][C:7]=1[Br:27]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 90290195tert-Butyl (S)-(1-(5-amino-3-bromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

Product 1

HCID 90290196tert-Butyl (S)-(1-(5-amino-3,6-dibromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of (S)-tert-butyl (1-(5-amino-3-bromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate (46A, 960 mg, 2.24 mmol) in 20 mL of acetonitrile was cooled to 0° C. and treated with N-bromosuccinimide (399 mg, 2.24 mmol) as a solution in 20 mL of acetonitrile. After 5 min, the reaction mixture was partitioned with EtOAc and saturated aqueous NaHCO3. The organic layer was separated and washed with brine, then dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with EtOAc/hexanes to afford the title product. MS (m/z): 507.52 [M+H]+.

Workup

  1. customthe reaction mixture was partitioned with EtOAc and saturated aqueous NaHCO3
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with EtOAc/hexanes

Sources & evidence

ORD record
ord-3390e77106244922b5fa086534c5ff4d
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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