Glycol monoethyl ether → 1,1,1-Trifluoro-2-[2-(1-phenyl-[1,2,4]triazolo[4,3-a]quinolin-7-ylsulfanyl)-thiazol-5-yl]-butan-2-ol

HRID 2075720Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][N:14]=[C:7]1[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].C(O[C:30](=O)[CH2:31][C:32]([OH:43])([C:37]1[S:41][C:40]([SH:42])=[N:39][CH:38]=1)[C:33]([F:36])([F:35])[F:34])C.CCOCCO>CC(O)C.CCOC(C)=O.O.[Cu](I)I>[F:36][C:33]([F:34])([F:35])[C:32]([C:37]1[S:41][C:40]([S:42][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]2[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[N:13][N:14]=[C:7]2[CH:6]=[CH:5]3)=[N:39][CH:38]=1)([OH:43])[CH2:31][CH3:30]

Participants

Conditions

Temperature: 90 °C

Procedure

7-Iodo-1-phenyl-[1,2,4]triazolo[4,3-a]quinoline (10c, 140 mg, 0.38 mmol), copper iodide (14 mg, 0.08 mmol), and potassium carbonate (105 mg, 0.76 mmol) were suspended in iPrOH (1 mL). 10b (92 mg, 0.38 mmol) in iPrOH (1 mL) was added, followed by ethyl glycol (0.04 mL, 0.76 mmol), and the reaction was heated to 90° C. overnight. The reaction was diluted with EtOAc and water, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (5% MeOH in CH2Cl2), and the isolated product was precipitated from CH2Cl2 to give the desired product, 10d.

Workup

extractionthe aqueous layer was extracted with EtOAc
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (5% MeOH in CH2Cl2)
customthe isolated product was precipitated from CH2Cl2

Sources & evidence

ORD record: ord-b99293a7aa1346f4922e1fa8c3d16d6e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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