Pyridine → Benzyl (4-chloropyridin-3-yl)carbamate

HRID 69950

반응식

HRID 69950 반응식
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[Cl:19].N1C=CC=CC=1>C1COCC1>[Cl:19][C:18]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[NH:12][C:2](=[O:3])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 5819323-Amino-4-chloropyridine

생성물 1

HCID 69042933Benzyl (4-chloropyridin-3-yl)carbamate수율 34%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of benzyl chloroformate (1.1 equiv.) in THF (1.85 M) was slowly added to a solution of 3-amino-4-chloropyridine (1.0 equiv.) and pyridine (1.5 equiv.) in THF (1.0 M) and stirred at rt for 3.5 hours (formation of a precipitate over time). The reaction was quenched with H2O (100 mL), extracted with EtOAc (200 mL), washed with NaCl(sat.) (75 mL), dried over MgSO4, filtered and the volatiles were removed in vacuo. The product precipitated from a mixture of hexane/EtOAc yielding benzyl 4-chloropyridin-3-ylcarbamate (34%). LCMS (m/z): 263.1 (MH+); LC Rt=2.33 min.

후처리

  1. customThe reaction was quenched with H2O (100 mL)
  2. extractionextracted with EtOAc (200 mL)
  3. washwashed with NaCl(sat.) (75 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe volatiles were removed in vacuo
  7. customThe product precipitated from a mixture of hexane/EtOAc

출처 및 근거

ORD 기록
ord-fe4cb553cd4346b4a655937987b025fe
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822497B2

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