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

HRID 271889

反応式

HRID 271889 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(C1C=CC(S([N:36]=[N+:37]=[N-:38])(=O)=O)=CC=1)CCCCCCCCCCC.[NH4+].[Cl-]>O1CCCC1>[N:36]([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+:37]=[N-:38]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 109151434-Dodecylbenzenesulfonyl azideHCID 22293237N-(5-Fluoropyridin-2-yl)pivalamide

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-butyl]ithium (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-6b88e919b8e04bb2b80c0a83cb4de6a4
出典データセット
uspto-grants-2008_11
特許番号
US07452903B2

関連ノート

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