Sodium Carbonate → HCID 22872657、化合物

HRID 1780348ノート

反応式

HRID 1780348 の反応式
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

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 22872666HCID 22872666、化合物

生成物 1

HCID 22872657HCID 22872657、化合物収率 68%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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 2M solution), and the mixture was heated at reflux for 1.5 hours. The solvent was removed under vacuum, and the residue was purified by chromotography on a silica gel column, eluting with hexane:ether 100:10-100:30 to afford of the title compound (345 mg, 68% yield). MS (DCI/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).

後処理

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

出典と根拠

ORDレコード
ord-c25a76b8f7dd4aa79d706844ddabe8bf
出典データセット
uspto-grants-1997_05
特許番号
US05629325

反応ノート

読み込み中…