ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate → HCID 21883569, compound

HRID 2297910Notes

Reaction equation

HRID 2297910 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[C:11](F)=[CH:12][C:13]2[O:18][CH:17]([C:19]([F:22])([F:21])[F:20])[C:16]([C:23]([O:25]CC)=[O:24])=[CH:15][C:14]=2[CH:28]=1>>[Cl:9][C:10]1[C:11]([O:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=2)=[CH:12][C:13]2[O:18][CH:17]([C:19]([F:21])([F:20])[F:22])[C:16]([C:23]([OH:25])=[O:24])=[CH:15][C:14]=2[CH:28]=1

Participants

3

Reactant 2

HCID 21883602ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylateHCID 1785160256-chloropyridin-2-ol

Product 1

HCID 21883569HCID 21883569, compound

Procedure

The title compound was prepared from 6-chloro-2-pyridinol and ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate (Example 183, Step 2) via a procedure similar to that described in Example 183, Steps 3 and 4: mp 226.4-227.4° C. 1H NMR (acetone-d6/300 MHz) 7.99 (m, 1H), 7.96 (s, 1H), 7.75 (s, 1H), 7.30 (d, 1H, J=7.7 Hz), 7.16 (d, 1H, J=8.0 Hz), 7.10 (s, 1H), 5.90 (q, 1H, J=7.0 Hz). 19F NMR (acetone-d6/282 MHz)−79.3 (d, J=7.2 Hz). FABLRMS m/z 404 (M−H). ESHRMS m/z 405.9853 (M+H, Calc'd 405.9861). Anal. Calc'd for C16H8Cl2F3NO4: C, 47.32; H, 1.99; N, 3.45; Cl, 17.46. Found: C, 47.26; H, 1.93; N, 3.35; Cl, 17.19.

Sources & evidence

ORD record
ord-4cab227c65254d8e93621f27ec6d4dc8
Source dataset
uspto-grants-2002_12
Patent number
US06492390B2

Reaction notes

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