Sodium Hydroxide → US10273222, Example 94

HRID 2277536Notes

Reaction equation

HRID 2277536 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[CH:9]=[CH:8][N:7]=2)[N:3]=[CH:2]1.[CH3:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([CH2:22][CH2:23]Br)=[CH:20][CH:19]=1.[OH-].[Na+]>CO>[CH3:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([CH2:22][CH2:23][N:1]2[CH:5]=[C:4]([C:6]3[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][N:7]=3)[N:3]=[CH:2]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 178498395methyl 2-(1H-imidazol-4-yl)pyridine-4-carboxylate

Product 1

HCID 86269287US10273222, Example 94Yield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared in 39% yield from methyl 2-(1H-imidazol-4-yl)pyridine-4-carboxylate (PREPARATION 5) and 4-methoxyphenethyl bromide according to the procedure for the preparation of Example 44, followed by saponification using NaOH in MeOH. 1HNMR (400 MHz, DMSO): δ 3.02 (2H, t, J=7.2 Hz), 3.71 (3H, s), 4.24 (2H, t, J=7.2 Hz), 6.83 (2H, t, J=8.6 Hz), 7.12 (2H, t, J=8.6 Hz), 7.58 (1H, d, J=3.7 Hz), 7.62 (1H, s), 7.82 (1H, s), 8.26 (1H, s), 8.63 (1H, d, J=4.9 Hz). [M+H] Calc'd for C18H17N3O3, 324. Found, 324.

Sources & evidence

ORD record
ord-46ed77eefb804a41985c4a8941c31b7c
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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