1H-Pyrazol-4-ol → 2-Methyl-4-[1-(tetrahydro-pyran-2-yl)-4-(tetrahydro-pyran-2-yloxy)-1H-pyrazol-3-yl]-quinolin-8-ol

HRID 1959612Notes

Reaction equation

HRID 1959612 reaction equation
[NH:1]1[CH:5]=[C:4]([OH:6])[CH:3]=[N:2]1.BrC1C=NC=C(Cl)C=1CO[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.Br[C:24]1[C:33]2[C:28](=[C:29]([OH:34])[CH:30]=[CH:31][CH:32]=2)[N:27]=[C:26]([CH3:35])[CH:25]=1.CC1C=C(C2N(C)C=CN=2)[C:44]2C(=[C:40]([OH:53])[CH:41]=[CH:42][CH:43]=2)N=1>>[CH3:35][C:26]1[CH:25]=[C:24]([C:5]2[C:4]([O:6][CH:44]3[CH2:43][CH2:42][CH2:41][CH2:40][O:53]3)=[CH:3][N:2]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:16][O:17]3)[N:1]=2)[C:33]2[C:28](=[C:29]([OH:34])[CH:30]=[CH:31][CH:32]=2)[N:27]=1

Participants

5

Reactant 4

HCID 1192181H-Pyrazol-4-olHCID 44190473HCID 44190473, compoundHCID 670771594-Bromo-2-methyl-quinolin-8-olHCID 1359503062-Methyl-4-(1-methyl-1H-imidazol-2-yl)-quinolin-8-ol

Product 1

HCID 1363463762-Methyl-4-[1-(tetrahydro-pyran-2-yl)-4-(tetrahydro-pyran-2-yloxy)-1H-pyrazol-3-yl]-quinolin-8-ol

Procedure

THP protection of 1H-Pyrazol-4-ol (420 mg. 2.06 mmol) according to the synthesis of 3-bromo-5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine subsequent coupling with 4-bromo-2-methyl-quinolin-8-ol according to the synthesis of 2-methyl-4-(1-methyl-1H-imidazol-2-yl)-quinolin-8-ol and flash chromatographic purification yielded the title compound. MS (m/z): 410.0 [M+H+].

Workup

  1. custompurification

Sources & evidence

ORD record
ord-a8b4ad7935a7471e87d6b559a8a738a9
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

Loading…