Water → [1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde

HRID 1432420ノート

反応式

HRID 1432420 の反応式
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[CH:9][N:10]=2)[CH:7]=1.C([Mg]Br)(C)C.CN([CH:19]=[O:20])C.O>C1COCC1>[N:10]1[CH:9]=[N:8][N:6]2[CH:7]=[C:2]([CH:19]=[O:20])[CH:3]=[CH:4][C:5]=12

参加物

6

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 177501416-Iodo-[1,2,4]triazolo[1,5-a]pyridineHCID 178418365HCID 178418365、化合物

生成物 1

HCID 45083592[1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde収率 101.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 6-iodo-[1,2,4]triazolo[1,5-a]pyridine (5.0 g, 20 mmol; prepared from 2-amino-5-iodopyridine (Aldrich-Sigma, St. Louis, Mo.) according to WO 01/62756) in anhydrous THF (300 mL) at 0° C. was slowly added a solution of isopropylmagnesium bromide in THF (1 M, 31 mL, 31 mmol). The resulting milky suspension was stirred at 0° C. After an hour, DMF (6 mL, 50 mmol) was added to the suspension at 0° C. and the suspension was allowed to warm up to room temperature and stirred for 4 additional hours. 100 mL of water was then added at room temperature and stirred for 1 hour. The resulting mixture was extracted with diethylether and washed with saturated Na2CO3. The extracts were dried over MgSO4 and concentrated. The residue was purified on a short silica gel cake with EtOAc to give [1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde as a light yellow solid (3 g, 100%). ESP+ m/e 148.0. 1H NMR (CDCl3, 300 MHz), δ 10.03 (s, 1H), 9.10 (s, 1H), 8.49 (s, 1H), 8.02 (d, 1H), 7.82 (d, 1H).

後処理

  1. waitAfter an hour
  2. temperatureto warm up to room temperature
  3. stirringstirred for 4 additional hours
  4. stirringstirred for 1 hour
  5. extractionThe resulting mixture was extracted with diethylether
  6. washwashed with saturated Na2CO3
  7. dry with materialThe extracts were dried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified on a short silica gel cake with EtOAc

出典と根拠

ORDレコード
ord-75767285c1e64fb08f515509d96d0a94
出典データセット
uspto-grants-2009_11
特許番号
US07612094B2

反応ノート

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