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

HRID 1629744노트

반응식

HRID 1629744 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-78baa8099b4c4e3f8fee0a0381d60c1b
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791100B2

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