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

HRID 513188Notes

Reaction equation

[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

Participants

Conditions

Temperature: 100 °C

Procedure

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).

Workup

customcap vial
customThe vial was capped
temperaturewas cooled to RT
filtrationThe mixture was filtered through Celite
washwashing with EtOAc
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-0b65b31eea264ac79712840ae875ce4e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102673B2

Reaction notes

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