Tert-Butylamine → N-tert-butyl-5-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridin-2-amine

HRID 628013

反応式

HRID 628013 の反応式
C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1.[I:22][C:23]1[CH:24]=[N+:25]([O-])[CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH2:31][C:32]1[CH:36]=[CH:35][S:34][CH:33]=1.[C:38]([NH2:42])([CH3:41])([CH3:40])[CH3:39]>C(Cl)(Cl)Cl>[C:38]([NH:42][C:26]1[CH:27]=[C:28]([O:29][CH2:30][CH2:31][C:32]2[CH:36]=[CH:35][S:34][CH:33]=2)[C:23]([I:22])=[CH:24][N:25]=1)([CH3:41])([CH3:40])[CH3:39]

参加物

5

反応物 3

HCID 6385Tert-Butylamine2 回HCID 77773Toluene-p-sulphonic anhydride2 回HCID 582840413-Iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine 1-oxide

生成物 1

HCID 57900152N-tert-butyl-5-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridin-2-amine

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

A solution of p-toluenesulfonic anhydride (1.47 g, 4.49 mmol) in 15 ml of chloroform was added dropwise to a stirred mixture of 0.78 g (2.25 mmol) of 3-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine 1-oxide and 1.18 ml (11.2 mmol) of tert-butylamine in 15 ml of chloroform at 0° C. After 30 minutes, the addition of the same quantities of p-toluenesulfonic anhydride and tert-butylamine was repeated to complete the reaction. The reaction mixture was concentrated and partitioned between 100 ml of diethylether and 1 M aqueous sodium carbonate. The aqueous layer was extracted with 50 ml of diethylether again and combined organic extracts were washed with water, brine, dried over sodium sulfate and concentrated in vacuum. The residue was purified by flash chromatography eluting with 10% of ethyl acetate in hexane to give N-tert-butyl-5-iodo-4-(2-(thiophen-3-yl)ethoxy)pyridin-2-amine (0.473 g (52%). 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 7.28 (dd, J=3.0, 4.8, 1H), 7.18 (s, 1H), 7.12 (d, J=4.9, 1H), 5.85 (s, 1H), 4.44 (s, 1H), 4.15 (t, J=6.5, 2H), 3.18 (t, J=6.5, 2H), 1.39 (s, 9H). MS: (ESI+) 403.2

後処理

  1. customthe reaction
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between 100 ml of diethylether and 1 M aqueous sodium carbonate
  4. extractionThe aqueous layer was extracted with 50 ml of diethylether again
  5. washwere washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified by flash chromatography
  9. washeluting with 10% of ethyl acetate in hexane

出典と根拠

ORDレコード
ord-d4250ecb26ff41b8bebad5dcd6124867
出典データセット
uspto-grants-2016_04
特許番号
US09309265B2

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