2-(Chloromethyl)-6-fluoroquinoline → 6-Fluoro-2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline hydrogen chloride

HRID 33845Notes

Reaction equation

HRID 33845 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[C:25]([C:26]5[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=5)=[CH:24][N:23]([CH3:32])[N:22]=4)=[CH:17][CH:16]=3)=[N:10]2)=[CH:5][CH:4]=1.ClCC1C=CC2C(=CC=C([F:45])C=2)N=1>>[ClH:2].[F:45][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:3]=1)[N:10]=[C:9]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]3[C:25]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)=[CH:24][N:23]([CH3:32])[N:22]=3)=[CH:17][CH:16]=1)[CH:8]=[CH:7]2

Participants

3

Reactant 2

HCID 112410072-(Chloromethyl)-6-fluoroquinolineHCID 115617317-Chloro-2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline hydrogen chloride

Product 1

HCID 116695066-Fluoro-2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline hydrogen chloride

Procedure

Following the procedure for the preparation of 7-Chloro-2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline hydrogen chloride but substituting 2-chloromethyl-6-fluoro-quinoline provided the title compound. 1H NMR (400 MHz, DMSO) δ 8.67 (d, J=6.6 Hz, 2H), 8.55 (s, 1 H), 8.42 (d, J=8.3, 1H), 8.04 (m, 1H), 7.82 (m, 1H), 7.71 (m, 4H), 7.36 (d, J=8.7 Hz, 2H), 7.12 (d, J=8.7, 2H), 5.37 (s, 2H), 3.91 (s, 3 H); MS: (M+H m/z=411.2).

Sources & evidence

ORD record
ord-18465de22eed4295b574d47f43af8c18
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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