8-Methyl-2-phenylquinoline-3-carboxaldehyde → HCID 67197756、化合物

HRID 1948728

反応式

HRID 1948728 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([CH:18]=[O:19])=[CH:7]2.[CH3:20][Li]>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:8]([CH:18]([OH:19])[CH3:20])=[CH:7]2

参加物

4

反応物 2

HCID 8336808-Methyl-2-phenylquinoline-3-carboxaldehydeHCID 178418348HCID 178418348、化合物2 回

生成物 1

HCID 67197756HCID 67197756、化合物収率 65%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 8-methyl-2-phenylquinoline-3-carboxaldehyde (211 mg, 0.85 mmol) in THF (6 mL) cooled to −78° C. was added methyllithium (1.6N solution in ether, 0.6 mL, 0.93 mmol). After 1 h a further portion of methyllithium (0.2 mL, 0.32 mmol) was added. The reaction was allowed to warm to r.t. before being quenched with water (10 mL). The THF was removed in vacuo and the residue partitioned between DCM (100 mL) and water (30 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 5-25% EtOAc in heptane) gave the title compound as a white solid (145 mg, 65%). δH (CDCl3) 8.42 (s, 1H), 7.70 (d, J 12 Hz, 1H), 7.60-7.63 (m, 2H), 7.42-7.55 (m, 5H), 5.23-5.31 (m, 1H), 2.80 (s, 3H), 1.87 (d, J 3.6 Hz, 1H), 1.47 (d, J 6.4 Hz, 3H). LCMS (ES+) 264.16 (M+H)+, RT 4.03 minutes (Method 4).

後処理

  1. custombefore being quenched with water (10 mL)
  2. customThe THF was removed in vacuo
  3. customthe residue partitioned between DCM (100 mL) and water (30 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (SiO2, 5-25% EtOAc in heptane)

出典と根拠

ORDレコード
ord-28319f5592994a859bd5d9a8b0630a8e
出典データセット
uspto-grants-2013_03
特許番号
US08399483B2

関連ノート

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