1h-Pyrrolo[2,3-c]pyridine-2-methanol,a-(4-methylphenyl)- → (4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

HRID 1821885ノート

反応式

HRID 1821885 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[NH:18][C:13]3=[CH:14][N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)[OH:9])=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[NH:18][C:13]3=[CH:14][N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)=[O:9])=[CH:6][CH:7]=1

参加物

4

反応物 1

HCID 578934571h-Pyrrolo[2,3-c]pyridine-2-methanol,a-(4-methylphenyl)-

生成物 1

HCID 57893512(4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone収率 67.1%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

(4-Methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (Example 98) (225 mg, 0.94 mmol) was dissolved in methylene chloride (15 mL). Manganese dioxide (817 mg, 9.40 mmol) was added and the reaction mixture was stirred for ca. 14 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed several times with hot ethanol. The filtrate was concentrated to give a white solid. Drying under vacuum produced (4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (149 mg, 67%) as a white solid: mp 264-268° C. dec.; 1H NMR (300 MHz, CD3OD) δ2.47 (3H, s), 7.18 (1H, s), 7.41 (2H, d, J=7.9 Hz), 7.73-7.75 (1H, m), 7.92 (2H, d, J=8.1 Hz), 8.16 (1H, d, J=5.6 Hz), 8.87 (1H, s); ESI MS m/z 237 [C15H12N2O+H]+; HPLC (Method A) 93.4% (AUC), tR=15.9 min.

後処理

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed several times with hot ethanol
  3. concentrationThe filtrate was concentrated
  4. customto give a white solid
  5. customDrying under vacuum

出典と根拠

ORDレコード
ord-b4a0acdea8374ba086525c42a273fefb
出典データセット
uspto-grants-2009_10
特許番号
US07608627B2

反応ノート

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