Sodium ethoxide → HCID 74223889, compound

HRID 623978Notes

Reaction equation

Cl[C:2]1[C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:10]([Cl:20])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:21]([C:33]3[N:37]([CH3:38])[CH:36]=[N:35][CH:34]=3)([C:23]3[CH:24]=[N:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=3)[OH:22])[CH:8]=2)[N:3]=1.[O-:39][CH2:40][CH3:41].[Na+]>>[Cl:20][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:21]([C:33]3[N:37]([CH3:38])[CH:36]=[N:35][CH:34]=3)([C:23]3[CH:24]=[N:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=3)[OH:22])[CH:8]=2)[N:3]=[C:2]([O:39][CH2:40][CH3:41])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1

Participants

Reactant 2

HCID 2723922Sodium ethoxide

HCID 74223798HCID 74223798, compound

Product 1

HCID 74223889HCID 74223889, compound

Procedure

The title compound was prepared using (2,4-dichloro-3-(4-fluorophenoxy)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanol (Example 11) in place of (4-chlorophenyl)(2,4-dichloro-3-phenoxyquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol (Example 1) according to the procedure of Example 2a except only one equivalent of sodium ethoxide was used. 1H NMR (400 MHz, MeOH-d4) δ 8.78 (d, J=1.96 Hz, 1H), 8.14 (d, J=1.96 Hz, 1H), 8.02 (dd, J=2.20, 8.31 Hz, 1H), 7.88 (d, J=8.56 Hz, 1H), 7.84 (d, J=8.31 Hz, 1H), 7.74 (s, 1H), 7.66 (dd, J=2.20, 8.80 Hz, 1H), 6.97-7.07 (m, 2H), 6.87 (dd, J=4.28, 9.17 Hz, 2H), 6.36 (s, 1H), 4.47 (q, J=7.09 Hz, 2H), 3.49 (s, 3H), 1.23 (t, J=7.09 Hz, 3H); MS m/e 574.2 [M+H]+.

Sources & evidence

ORD record: ord-01849aaee16d4e478eeb6af6ef3547a3
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303015B2

Reaction notes

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