Trimethyl orthoformate → 2-Bromo-5-chloro-4-(dimethoxymethyl)pyridine

HRID 1629744ノート

反応式

HRID 1629744 の反応式
[Br:1][C:2]1[N:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1C=O.[CH3:11][O:12][CH:13](OC)[O:14][CH3:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:6]([CH:13]([O:14][CH3:15])[O:12][CH3:11])[C:7]([Cl:10])=[CH:8][N:9]=1

参加物

6

反応物 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 575173392-Bromo-5-chloropyridine-3-carbaldehyde

生成物 1

HCID 575173382-Bromo-5-chloro-4-(dimethoxymethyl)pyridine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-bromo-5-chloronicotinaldehyde (3.00 g, 13.6 mmol), trimethylorthoformate (4.48 mL, 40.8 mmol) and p-toluenesulfonic acid monohydrate (129 mg, 0.680 mmol) in MeOH (55 mL) was refluxed for 16 hours. The mixture was diluted in CH2Cl2 and washed with 10% aqueous potassium carbonate and brine, dried over sodium sulfate, filtered and concentrated. The crude product was used in the next step without further purification. LC/MS method 2: MS (ESI): 267 [M+H]+, rt=2.22 min. 1H-NMR (DMSO-d6): δ (ppm) 8.53 (s, 1H), 7.65 (S, 1H), 5.53 (s, 1H), 3.31 (2d, 6H).

後処理

  1. temperaturewas refluxed for 16 hours
  2. washwashed with 10% aqueous potassium carbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was used in the next step without further purification
  7. custom267 [M+H]+, rt=2.22 min

出典と根拠

ORDレコード
ord-78baa8099b4c4e3f8fee0a0381d60c1b
出典データセット
uspto-grants-2014_07
特許番号
US08791100B2

反応ノート

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