Sodium hydride → HCID 67373425、化合物

HRID 1253547ノート

反応式

HRID 1253547 の反応式
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

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 67207447HCID 67207447、化合物

生成物 1

HCID 67373425HCID 67373425、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-469fb0c300ca4229bfbb91ab7061dc82
出典データセット
uspto-grants-2013_06
特許番号
US08455477B2

反応ノート

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