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

HRID 2170383ノート

反応式

HRID 2170383 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-3390e77106244922b5fa086534c5ff4d
出典データセット
uspto-grants-2015_06
特許番号
US09050344B2

反応ノート

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