Potassium Hydroxide → HCID 86760732, compound

HRID 2116661Notes

Reaction equation

[OH-:1].[K+].[F:3][C:4]([F:16])([F:15])[C@:5]([C:9]1[S:13][C:12]([SH:14])=[N:11][CH:10]=1)(O)[CH2:6][CH3:7].Br[C:18]1[CH:27]=[C:26]2[C:21]([C:22]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)=[CH:23][C:24](=[O:28])[O:25]2)=[CH:20][CH:19]=1>CO.CN1C(=O)CCC1>[OH:1][CH2:7][CH2:6][C@@H:5]([C:9]1[S:13][C:12]([S:14][C:18]2[CH:27]=[C:26]3[C:21]([C:22]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:23][C:24](=[O:28])[O:25]3)=[CH:20][CH:19]=2)=[N:11][CH:10]=1)[C:4]([F:16])([F:15])[F:3]

Participants

Conditions

Temperature: 120 °C

Procedure

KOH (0.223 g, 3.97 mmol) was added to a solution of (2R)-1,1,1-trifluoro-2-(2-mercapto-1,3-thiazol-5-yl)butan-2-ol (0.966 g, 3.97 mmol) in dry MeOH. When a solution was obtained, the reaction mixture was concentrated to dryness. Dry toluene was then added and the mixture was concentrated to dryness again. The residue was dissolved with 7-bromo-4-pyridin-3-yl-2H-chromen-2-one (1.0 g, 3.31 mmol) in NMP, and the resulting mixture was stirred at 120° C. for 16 h. Once cooled, the mixture was directly applied onto a column of silica gel and chromatographed (acetone/toluene; 5:95 to 15:85), affording the title compound. 1H NMR (400 MHz, CDCl3): δ 8.81 (dd,1H), 8.72 (dd, 1H), 7.82 (dt, 1H), 7.78 (s, 1H), 7.51-7.59 (m, 2H), 7.33-7.40 (m, 2H), 6.42 (s, 1H), 2.88 (br s, 1H), 2.12 (q, 2H), 0.99 (t, 3H).

Workup

customWhen a solution was obtained
concentrationthe reaction mixture was concentrated to dryness
additionDry toluene was then added
concentrationthe mixture was concentrated to dryness again
temperatureOnce cooled
customchromatographed (acetone/toluene; 5:95 to 15:85)

Sources & evidence

ORD record: ord-2e40798ca1194e008a5d0ed2827612fa
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439260B2

Reaction notes

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