Sodium hydride → HCID 67373425, 화합물

HRID 1253547노트

반응식

HRID 1253547 반응식
Br[C:2]1[CH:3]=[C:4]([OH:11])[C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=1.Br.Br[CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[H-].[Na+]>CN(C=O)C>[CH3:7][N:6]1[CH:5]=[C:10]([C:2]2[CH:3]=[C:4]([O:11][CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[C:5]3[N:6]([N:8]=[CH:9][CH:10]=3)[CH:7]=2)[CH:9]=[N:8]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 67207447HCID 67207447, 화합물

생성물 1

HCID 67373425HCID 67373425, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-bromopyrazolo[1,5-a]pyridin-4-ol (10.0 mg, 0.047 mmol), 3-(bromomethyl)pyridine hydrobromide (14.2 mg, 0.056 mmol), and NaH (6.7 mg, 0.168 mmol, 60 wt %) were suspended in DMF (1 ml) and stirred for 1 h. The reaction mixture was quenched by the addition of saturated aqueous ammonium chloride. The reaction mixture was diluted in ethyl acetate, then washed with water (5 mL) and brine (5 mL). The combined aqueous layers were extracted with ethyl acetate (2×10 mL), and the combined organic layers were dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient) to afford 6-(1-methyl-1H-pyrazol-4-yl)-4-(pyridin-3-ylmethoxy)pyrazolo[1,5-a]pyridine.

후처리

  1. customThe reaction mixture was quenched by the addition of saturated aqueous ammonium chloride
  2. additionThe reaction mixture was diluted in ethyl acetate
  3. washwashed with water (5 mL) and brine (5 mL)
  4. extractionThe combined aqueous layers were extracted with ethyl acetate (2×10 mL)
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-469fb0c300ca4229bfbb91ab7061dc82
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455477B2

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