Sodium Hydroxide → US10273222, Example 92

HRID 2277534Notes

Reaction equation

HRID 2277534 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][C:20]([CH2:21][CH2:22]Br)=[CH:19][CH:18]=1.[OH-].[Na+]>CO>[F:16][C:17]1[CH:25]=[CH:24][C:20]([CH2:21][CH2:22][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:19][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5731534-Fluorophenethyl bromideHCID 178498395methyl 2-(1H-imidazol-4-yl)pyridine-4-carboxylate

Product 1

HCID 86269285US10273222, Example 92Yield 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 4-fluorophenethyl bromide according to the procedure for the preparation of Example 44, followed by saponification using NaOH in MeOH. 1HNMR (400 MHz, DMSO): δ 3.09 (2H, t, J=7.1 Hz), 4.27 (2H, t, J=7.2 Hz), 7.11 (2H, t, J=8.8 Hz), 7.24 (2H, t, J=7.1 Hz), 7.57 (1H, d, J=3.8 Hz), 7.63 (1H, s), 7.82 (1H, s), 8.26 (1H, s), 8.63 (1H, d, J=5.0 Hz). [M+H] Calc'd for C17H14FN3O2, 312. Found, 312.

Sources & evidence

ORD record
ord-ed0078ad5dfe480795467e62c384c959
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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