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

HRID 1432420노트

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HRID 1432420 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-75767285c1e64fb08f515509d96d0a94
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612094B2

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