4-Hydroxybenzaldehyde → 2-Fluoro-4-{3-[5-(4-hydroxy-benzyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl]-1H-indazol-6-yl}-5-(2,2,2-trifluoro-ethyl)-phenol

HRID 340047Notes

Reaction equation

HRID 340047 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:17]4[NH:18][C:19]5[CH2:24][CH2:23][NH:22][CH2:21][C:20]=5[N:25]=4)=[N:13][NH:14]3)=[CH:10][CH:9]=2)[C:5]([CH2:26][C:27]([F:30])([F:29])[F:28])=[CH:4][C:3]=1[OH:31].[OH:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1>>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:17]4[NH:18][C:19]5[CH2:24][CH2:23][N:22]([CH2:37][C:36]6[CH:39]=[CH:40][C:33]([OH:32])=[CH:34][CH:35]=6)[CH2:21][C:20]=5[N:25]=4)=[N:13][NH:14]3)=[CH:10][CH:9]=2)[C:5]([CH2:26][C:27]([F:28])([F:29])[F:30])=[CH:4][C:3]=1[OH:31]

Participants

3

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 1785160382-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-5-(2,2,2-trifluoro-ethyl)-phenol

Product 1

HCID 1785160782-Fluoro-4-{3-[5-(4-hydroxy-benzyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl]-1H-indazol-6-yl}-5-(2,2,2-trifluoro-ethyl)-phenol

Procedure

The title compound was prepared from 2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-5-(2,2,2-trifluoro-ethyl)-phenol (100 mg, 0.21 mmol) and 4-hydroxybenzaldehyde (56.6 mg, 0.46 mmol) using the method of Example 51. The crude material was purified initially over silica and finally by Prep TLC (Mobile Phase: 10% MeOH-DCM) to afford the title compound as an off white solid in 24.4% yield, 28 mg.

Workup

  1. customThe crude material was purified initially over silica and finally by Prep TLC (Mobile Phase: 10% MeOH-DCM)

Sources & evidence

ORD record
ord-bf1761abf5314fb9a8e7153cb6b60e61
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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