Potassium Carbonate → Methyl 4-(3-methoxyphenyl)-1-(3-phenylpropyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

HRID 513188ノート

反応式

HRID 513188 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]3[CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[NH:17][C:13]=3[CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1.Br[CH2:35][CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]3[CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[N:17]([CH2:35][CH2:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:13]=3[CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 312751,4-DioxaneHCID 71212598methyl 4-(3-methoxyphenyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

生成物 1

HCID 86720569Methyl 4-(3-methoxyphenyl)-1-(3-phenylpropyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate収率 96%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

Methyl 4-(3-methoxyphenyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (50 mg, 0.177 mmole) and K2CO3 (49.0 mg, 0.354 mmole) were combined in a screw cap vial. To this was added 1,4-dioxane (0.75 mL) and 1-bromo-3-phenylpropane (0.035 mL, 0.230 mmole). The vial was capped then heated to 100° C. After stirring overnight the mixture was cooled to RT and diluted with EtOAc. The mixture was filtered through Celite washing with EtOAc. The filtrate was concentrated. Flash column (Biotage-SNAP-10 g SiO2, 30% EtOAc/hexanes) gave the title compound (68 mg, 96%) as a pale yellow oil. 1H NMR (399 MHz, CDCl3): δ 8.46 (d, J=6.0 Hz, 1 H); 7.58 (d, J=1.0 Hz, 1 H); 7.55-7.50 (m, 2 H); 7.48-7.39 (m, 1 H); 7.32-7.27 (m, 2H); 7.23-7.17 (m, 3 H); 7.09 (dd, J=6.0, 1.0 Hz, 1 H); 7.02 (ddd, J=8.2, 2.7, 1.1 Hz, 1 H); 4.65-4.57 (m, 2 H); 3.91 (m, 6 H); 2.76-2.68 (m, 2 H); 2.21-2.13 (m, 2 H).

後処理

  1. customcap vial
  2. customThe vial was capped
  3. temperaturewas cooled to RT
  4. filtrationThe mixture was filtered through Celite
  5. washwashing with EtOAc
  6. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-0b65b31eea264ac79712840ae875ce4e
出典データセット
uspto-grants-2015_08
特許番号
US09102673B2

反応ノート

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