Ammonium Chloride → N-(3-Azido-5-fluoropyridin-2-yl)-2,2-dimethylpropanamide

HRID 501090

反応式

HRID 501090 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.C([Li])(C)(C)C.C(C1C=CC(S([N:41]=[N+:42]=[N-:43])(=O)=O)=CC=1)CCCCCCCCCCC.[NH4+].[Cl-]>O1CCCC1>[N:41]([C:4]1[C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12])=[N:6][CH:7]=[C:2]([F:1])[CH:3]=1)=[N+:42]=[N-:43]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 109151434-Dodecylbenzenesulfonyl azideHCID 22293237N-(5-Fluoropyridin-2-yl)pivalamideHCID 178418306HCID 178418306、化合物

生成物 1

HCID 22293288N-(3-Azido-5-fluoropyridin-2-yl)-2,2-dimethylpropanamide収率 17%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a −78° C. solution of N-(5-fluoropyridin-2-yl)-2,2-dimethylpropanamide (1.34 g, 6.83 mmol) in tetrahydrofuran (25 mL) was added tert-butyllithium (1.31 mL of a 1.7 M solution, 20.5 mmol) drop wise. After 3 h at −78° C., 4-dodecylbenzenesulfonyl azide (3.60 g, 10.2 mmol) was added at the reaction was allowed to warm to room temperature. After 1 h, saturated aqueous NH4Cl was added, and the tetrahydrofuran was removed via rotary evaporator. Dichloromethane was added, the layers separated and the aqueous phase backwashed with DCM. The combined organics were dried over magnesium sulfate, filtered and concentrated and the residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes, then 5%→42% EtOAc/hexanes) to give the title compound (0.275 g). MS 234.0 (M+1).

後処理

  1. waitAfter 1 h
  2. customthe tetrahydrofuran was removed via rotary evaporator
  3. additionDichloromethane was added
  4. customthe layers separated
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes

出典と根拠

ORDレコード
ord-4ee6ccd0ba0c40cca88a605c0a83f5b2
出典データセット
uspto-grants-2010_08
特許番号
US07772224B2

関連ノート

読み込み中…