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

HRID 1780336노트

반응식

HRID 1780336 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 2M 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:ether 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-c9367e30a8594a189363c648975f4d7b
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05629325

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