Sodium Carbonate → 5-(3-aminophenyl)-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine

HRID 365838노트

반응식

HRID 365838 반응식
Br[C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[N:6][CH:7]=1.[NH2:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[NH2:21][C:22]1[CH:27]=[C:26]([C:2]2[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]3[CH2:13][CH2:12][N:11]3[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[N:6][CH:7]=2)[CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 10688713(S)-Tert-butyl 2-(((5-bromopyridin-3-YL)oxy)methyl)azetidine-1-carboxylate

생성물 1

HCID 228726525-(3-aminophenyl)-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine수율 41.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

The 5-bromo-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from Example 54b (400 mg, 1.2 mmol), 3-aminophenylboronic acid (361 mg, 2.3 mmol, Aldrich Chem. Co.), Pd(0) (35 mg) and Na2CO3 (1.5 mL of a 2 M solution) were mixed in 8 mL of toluene, and the mixture was stirred at reflux for 16 hours. The solvent was removed under vacuum, and the residue was purified by chromatography on silica gel, eluting with exane:Et2O 1:1, to afford 178 mg of the title compound. MS (CI/NH3) m/z 356 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.42 (s, 9H), 2.33 (m, 2H), 3.92 (m, 2H), 4.20 (m, 1H), 4.38 (m, 1H), 4.55 (m, 1H), 6.72 (m, 1H), 6.88 (s, 1H), 6.97 (m, 1H), 7.44 (m, 2H), 8.31 (m, 1H), 8.44 (m, 1H).

후처리

  1. temperatureat reflux for 16 hours
  2. customThe solvent was removed under vacuum
  3. customthe residue was purified by chromatography on silica gel
  4. washeluting with exane

출처 및 근거

ORD 기록
ord-fd225e79779f4390adf48c296fe0ed6c
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127386

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