3-(Trifluoromethyl)pyrazole → 7-methoxy-4-(4-methoxy-benzyloxy)-8-methyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinoline

HRID 880774Notes

Reaction equation

HRID 880774 reaction equation
Cl[C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:9]2[C:4](=[C:5]([CH3:24])[C:6]([O:22][CH3:23])=[CH:7][CH:8]=2)[N:3]=1.[F:25][C:26]([F:33])([F:32])[C:27]1[CH:31]=[CH:30][NH:29][N:28]=1.ClC1C(OC)=CC=C2C=1N=C(N1C=CC(C(F)(F)F)=N1)C=C2OCC1C=CC(OC)=CC=1>>[CH3:23][O:22][C:6]1[C:5]([CH3:24])=[C:4]2[C:9]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:11][C:2]([N:29]3[CH:30]=[CH:31][C:27]([C:26]([F:33])([F:32])[F:25])=[N:28]3)=[N:3]2)=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 18070343-(Trifluoromethyl)pyrazoleHCID 566051548-chloro-7-methoxy-4-(4-methoxy-benzyloxy)-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinolineHCID 566051592-Chloro-8-methyl-7-methoxy-4-(4-methoxy-benzyloxy)-quinoline

Product 1

HCID 566051607-methoxy-4-(4-methoxy-benzyloxy)-8-methyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinolineYield 19%

Procedure

7-Methoxy-4-(4-methoxy-benzyloxy)-8-methyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinoline 234c was synthesized from compounds 221b and 233a, following the procedure as described for compound 234a, as a white solid in 19% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.64 (s, 3H), 3.86 (s, 3H), 3.99 (s, 3H), 5.33 (s, 2H), 6.75 (d, J=2.58 Hz, 1H), 6.98 (d, J=8.78 Hz, 2H), 7.20 (d, J=9.22 Hz, 1H), 7.48 (d, J=8.78 Hz, 2H), 7.57 (s, 1H), 8.07 (d, J=9.08 Hz, 1H), 8.88 (s, 1H).

Sources & evidence

ORD record
ord-c1957bcede5c4abcbf2715917ee55585
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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