Sodium Hydroxide → 7-(pyridin-3-ylcarbonyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid

HRID 854885Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:23]([O:25]CC)=[O:24])[CH:15]([C:19]([F:22])([F:21])[F:20])[O:16]3)=[CH:11][CH:10]=2)=[O:8])[CH:2]=1.[OH-].[Na+]>CO.C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:23]([OH:25])=[O:24])[CH:15]([C:19]([F:21])([F:22])[F:20])[O:16]3)=[CH:11][CH:10]=2)=[O:8])[CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The ester from Step 1 (38 mg, 0.08 mmole) was dissolved in 0.5 mL methanol and 0.5 mL THF. Sodium hydroxide (2.5 N) (0.2 mL, 0.5 mmole) was added to above solution and stirred at 50° C. for 4 h. The crude was purified by RPHPLC with 45% ACN in water to afford a white solid (15 mg,41%): LCMS m/z 350.05 (M+H). 1H NMR (DMSO-d6/400 MHz) 8.87 (s, 1H), 8.83 (d, 1H, J=6.8 Hz), 8.11 (d, 1H, J=10.4 Hz), 7.94 (s,1H), 7.69 (d, 1H, J=14 Hz), 7.60 (m, 1H), 7.42 (d, 1H, J=10.4 Hz), 7.34 (s, 1H), 6.03 (q, 1H, J=9.6 Hz).

Workup

customThe crude was purified by RPHPLC with 45% ACN in water

Sources & evidence

ORD record: ord-06eec45ad51e4703a1f245eb8655fee9
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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