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

HRID 2410731

반응식

HRID 2410731 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

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온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-13c70ab19bb24840948bccf4af426e52
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815840B2

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