Pyridine → HCID 22905634、化合物

HRID 1488458ノート

反応式

HRID 1488458 の反応式
[OH:1][C:2]1[C:3]([CH3:13])=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][CH2:6][CH:5]2[CH3:12].N1C=CC=CC=1.[C:20](Cl)(=[O:24])[CH:21]([CH3:23])[CH3:22]>C(Cl)Cl>[C:20]([N:7]1[C:8]2[C:4](=[C:3]([CH3:13])[C:2]([OH:1])=[C:10]([CH3:11])[CH:9]=2)[CH:5]([CH3:12])[CH2:6]1)(=[O:24])[CH:21]([CH3:23])[CH3:22]

参加物

5

反応物 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 22905653HCID 22905653、化合物

生成物 1

HCID 22905634HCID 22905634、化合物収率 73.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To an ice-cold solution of indoline 10 (160 mg, 0.9 mmol) dissolved in methylene chloride (4 mL) and kept under an argon atmosphere were added sequentially pyridine (1 mL) and isobutyryl chloride (0.I mL, 9 mmol); the mixture was stirred over the range of 0° C. to room temperature for some 17 h. The mixture was diluted with methylene chloride, washed with brine and dried (MgSO4). Removal of solvents followed by purification of the residue using 1:9 ethyl acetate:hexanes as eluent afforded the desired N-isobutyryl-5-hydroxy-3,4,6-trimethylindoline (11b, 163 mg, 73% yield) as a colorless solid, mp 123°-125° C. Spectral data: 1H NMR: δ1.1-1.25 (m, 9H), 2.17 (s, 3H), 2.20 (s, 3H), 2.72 (quintet, 1H, J=6.5 Hz), 3.35 (t, 1H, J=6.5 Hz), 3.78 (dd, 1H, J=10.1, 1.0 Hz), 4.13 (t, 1H, J=9.1 Hz), 7.95 (s, 1H); 13C NMR: δ 11.9, 16.5, 18.8, 19.3, 20.7, 33.1, 34.0, 56.3, 116.8, 119.5, 122.1, 134.1, 135.0, 148.8, 175.0; HRMS: calcd. for C15H21NO2 247.1523, fnd. 247.1573. Anal: calcd. for C15H21NO2C, 72.85, H, 8.55, N, 5.66, fnd. C, 72.63, H, 8.59, N, 5.60.

後処理

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customRemoval of solvents
  4. customfollowed by purification of the residue

出典と根拠

ORDレコード
ord-fc3887e276024ae9bd645069b917c0d0
出典データセット
uspto-grants-1997_10
特許番号
US05674876

反応ノート

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