Dimethylformamide → 7-Methyl-6-(pyridin-3-yl) imidazo[1,2-a]pyridine-3-carbaldehyde

HRID 401451

反応式

HRID 401451 の反応式
Br[C:2]1[C:3]([CH3:13])=[CH:4][C:5]2[N:6]([C:8]([CH:11]=[O:12])=[CH:9][N:10]=2)[CH:7]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>C(OCC)(=O)C>[CH3:13][C:3]1[C:2]([C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)=[CH:7][N:6]2[C:8]([CH:11]=[O:12])=[CH:9][N:10]=[C:5]2[CH:4]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 467391706-Bromo-7-methylimidazo[1,2-a]pyridine-3-carbaldehyde2 回

生成物 1

HCID 866705967-Methyl-6-(pyridin-3-yl) imidazo[1,2-a]pyridine-3-carbaldehyde収率 62%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

6-bromo-7-methylimidazo[1,2-a]pyridine-3-carbaldehyde (Compound of step 1, 2000 mg, 7.90 mmol), Pyridine-3-boronic acid (1170 mg, 9.49 mmol), dichlorobis (triphenylphosphine) palladium (II) (200 mg, 10% mmol) and 2M aqueous Na2CO3 (7 mL) were added to DMF (25 mL) and refluxed for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with H2O and brine. The solvent was evaporated to obtain crude product, which was purified by column chromatography (silica gel, 1% methanol in chloroform) to obtain the title compound. Yield: 62%; 1H NMR (DMSO-d6; 300 MHz): δ 9.92 (s, 1H), 9.20 (s, 1H), 8.69-8.70 (m, 2H), 8.54 (s, 1H), 7.95-7.99 (m, 1H), 7.90 (s, 1H), 7.53-7.58 (m, 1H), 2.34 (s, 3H); MS: m/z 238 (M+1)+

後処理

  1. temperaturerefluxed for 2 hours
  2. washwashed with H2O and brine
  3. customThe solvent was evaporated
  4. customto obtain crude product, which
  5. customwas purified by column chromatography (silica gel, 1% methanol in chloroform)

出典と根拠

ORDレコード
ord-f793354b8d7045b88172a688a1b6cc8d
出典データセット
uspto-grants-2014_06
特許番号
US08741932B2

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