Sodium Carbonate → HCID 22872654, 화합물

HRID 365848노트

반응식

HRID 365848 반응식
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[N:6][C:7]=1[Cl:8].[NH2:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[NH2:23][C:24]1[CH:29]=[C:28]([C:2]2[CH:3]=[C:4]([O:9][CH2:10][C@H:11]3[CH2:15][CH2:14][CH2:13][N:12]3[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[N:6][C:7]=2[Cl:8])[CH:27]=[CH:26][CH:25]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 22872666HCID 22872666, 화합물

생성물 1

HCID 22872654HCID 22872654, 화합물수율 29.8%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 5-bromo-6-chloro-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine from Example 69a (520 mg, 1.33 mmol) and 3-aminophenylboronic acid (310 mg, 2.0 mmol) in toluene (8 mL) was added Pd(0) (50 mg) and Na2CO3 (2.5 mL of a 2 M solution), and the mixture was heated at reflux for 16 hours. The solvent was removed under vacuum, and the residue was purified by chromatography on a silica gel column, eluting with CHCl3 :Et2O 100:5-100:40 to afford 160 mg of the title compound. MS (CI/NH3) m/z 404 (M+H)+. 1H NMR (CDC13, 300 MHz) δ1.44 (s, 9H), 1.88 (m, 1H), 2.03 (m, 2H), 3.37 (m, 2H), 3.76 (m, 2H), 4.16 (m, 2H), 6.75 (m, 2H), 6.82 (m, 1H), 7.22 (m, 2H), 8.08 (m, 1H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromatography on a silica gel column
  5. washeluting with CHCl3 :Et2O 100:5-100:40

출처 및 근거

ORD 기록
ord-eae4f0db95f84fa490224f6b650d5d20
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127386

반응 노트

불러오는 중…