Acetic Acid → tert-Butyl 6-bromo-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate

HRID 225847노트

반응식

HRID 225847 반응식
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O)=O.C1C(=O)N([Br:29])C(=O)C1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Br:29])=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 11831362tert-Butyl 3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate

생성물 1

HCID 11833959tert-Butyl 6-bromo-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(tert-butoxycarbonyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (1.37 g, 5.85 mmole) in CH2Cl2 (30 mL) was added glacial HOAc (3.4 mL, 58.5 mmole) and NBS (1.09 g, 6.14 mmole). After 72 hr the mixture was washed with 2.0 M NaOF, H2O, and brine. The mixture was dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound (1.79 g, 98%) which was sufficiently pure for use in the next step: 1H NMR (400 MHz, CDCl3) δ 8.35 (s, 1 H), 7.51 (s, 1 H), 3.77 (m, 2 H), 2.75 (t, J=6.5 Hz, 2 H), 1.93 (m, 2 H), 1.54 (s, 9 H).

후처리

  1. washAfter 72 hr the mixture was washed with 2.0 M NaOF, H2O, and brine
  2. dry with materialThe mixture was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-58fa3a77db1f45cb863eed42ab085058
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557125B2

반응 노트

불러오는 중…