Potassium Phosphate, Tribasic → methyl 8-chloro-7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate

HRID 2410731

反応式

HRID 2410731 の反応式
C1(P(C2CCCCC2)C2C=CC=CC=2[C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=2OC)CCCCC1.COC1C=CC(B(O)O)=CC=1.Br[C:42]1[CH:43]=[C:44]([C:58]([O:60][CH3:61])=[O:59])[C:45]2[NH:46][C:47]3[CH:48]=[C:49]([O:56][CH3:57])[C:50]([Cl:55])=[CH:51][C:52]=3[C:53]=2[N:54]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:55][C:50]1[C:49]([O:56][CH3:57])=[CH:48][C:47]2[NH:46][C:45]3[C:44]([C:58]([O:60][CH3:61])=[O:59])=[CH:43][C:42]([C:16]4[CH:15]=[CH:14][C:19]([O:20][CH3:21])=[CH:18][CH:17]=4)=[N:54][C:53]=3[C:52]=2[CH:51]=1

参加物

6

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 201262(4-Methoxyphenyl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86663015methyl 2-bromo-8-chloro-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate

生成物 1

HCID 66604816methyl 8-chloro-7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate収率 487.2%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
80 °C

実験手順

A vial containing dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (6 mg, 0.015 mmol), 4-methoxyphenylboronic acid (14 mg, 0.093 mmol), methyl 2-bromo-8-chloro-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate (29 mg, 0.077 mmol), palladium(II) acetate (1.7 mg, 7.7 μmol), and potassium phosphate tribasic (49.1 mg, 0.231 mmol) was flushed with nitrogen. Tetrahydrofuran (1 mL) was added and the reaction was heated at 80° C. overnight. The reaction was partitioned between EtOAc and water. The organic phase was separated, washed with brine, dried with sodium sulfate, and the solvents removed. Radial silica gel chromatography (elution with DCM) afforded methyl 8-chloro-7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (29 mg). MS (ESI) m/z 397.0 (M+H). 1H NMR (CDCl3) δ ppm 9.31 (1H, s), 8.31 (1H, s), 8.00-8.12 (3H, m), 6.99-7.07 (2H, m), 6.90 (1H, s), 4.03 (3H, s), 3.96 (3H, s), 3.88 (3H, s).

後処理

  1. customwas flushed with nitrogen
  2. additionTetrahydrofuran (1 mL) was added
  3. customThe reaction was partitioned between EtOAc and water
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried with sodium sulfate
  7. customthe solvents removed
  8. washRadial silica gel chromatography (elution with DCM)

出典と根拠

ORDレコード
ord-13c70ab19bb24840948bccf4af426e52
出典データセット
uspto-grants-2014_08
特許番号
US08815840B2

関連ノート

読み込み中…