Sodium Carbonate → HCID 22872657, 화합물

HRID 365849노트

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HRID 365849 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].[Cl:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([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:26][CH:25]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 22872666HCID 22872666, 화합물

생성물 1

HCID 22872657HCID 22872657, 화합물수율 68%

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 (460 mg, 1.2 mmol) and 4-chlorophenylboronic acid (225 mg, 1.44 mmol) in toluene (10 mL) was added Pd(0) (40 mg) and Na2CO3 (1.2 mL of a 2 M solution), and the mixture was heated at reflux for 1.5 hours. The solvent was removed under vacuum, and the residue was purified by chromatography on a silica gel column, eluting with hexane:Et2O 100:10-100:30 to afford of the title compound (345 mg, 68% yield). MS (CI/NH3) m/z 423 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.45 (s, 9H), 1.89 (m, 2H), 2.03 (m, 2H), 3.37 (m, 2H), 4.00 (m, 1H), 4.15 (m, 2H), 7.42 (m, 6H), 8.10 (m, 2H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromatography on a silica gel column
  5. washeluting with hexane:Et2O 100:10-100:30

출처 및 근거

ORD 기록
ord-dd17a1ee053b48ee8d9edc37eab9d3ae
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127386

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