Sodium Hydroxide → US10273222, Example 93

HRID 2277535Notes

Reaction equation

HRID 2277535 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.[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][CH2:20]Br.[OH-].[Na+]>CO>[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][CH2:20][N:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][N:7]=2)[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27569642-Fluorophenethyl bromideHCID 178498395methyl 2-(1H-imidazol-4-yl)pyridine-4-carboxylate

Product 1

HCID 86269286US10273222, Example 93Yield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared in 48% yield from methyl 2-(1H-imidazol-4-yl)pyridine-4-carboxylate (PREPARATION 5) and 2-fluorophenethyl bromide according to the procedure for the preparation of Example 44, followed by saponification using NaOH in MeOH. 1HNMR (400 MHz, DMSO): δ 3.14 (2H, t, J=6.9 Hz), 4.29 (2H, t, J=7.0 Hz), 7.13 (2H, m), 7.27 (2H, m), 7.58 (1H, d, J=4.0 Hz), 7.63 (1H, s), 7.80 (1H, s), 8.25 (1H, s), 8.62 (1H, d, J=4.9 Hz). [M+H] Calc'd for C17H14FN3O2, 312. Found, 312.

Sources & evidence

ORD record
ord-26bc6ecb7dee42e39b0e2bdeb6841d7b
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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