1,10-Phenanthroline → HCID 68380034, compound

HRID 2364966Notes

Reaction equation

C[O:2][C:3]1[C:11]2[S:10][C:9]([C:12]([F:15])([F:14])[F:13])=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.BrC1C(OC)=CC=CC=1NC(=S)C(F)(F)F.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.[Cu](I)I>[F:15][C:12]([F:13])([F:14])[C:9]1[S:10][C:11]2[C:3]([OH:2])=[CH:4][CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Synthesis of 7-methoxy-2-(trifluoromethyl)-1,3-benzothiazole (C26). To a solution of N-(2-bromo-3-methoxyphenyl)-2,2,2-trifluoroethanethioamide (C25) (748 mg, 2.38 mmol) in 1,2-dimethoxyethane (11.9 mL) was added 1,10-phenanthroline (88.4 mg, 0.48 mmol), cesium carbonate (1.55 g, 4.76 mmol), and copper iodide (45.3 mg, 0.24 mmol). Nitrogen was bubbled through the reaction for 30 minutes and the reaction was heated to 80° C. for 48 hours. The mixture was cooled to room temperature, filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 30% diethyl ether in hexanes) afforded the title compound as a colorless solid. Yield: 398 mg, 1.71 mmol, 72%. GCMS m/z 233 (M+). 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 3H), 6.97 (br d, J=7.9 Hz, 1H), 7.56 (dd, J=8.3, 8.0 Hz, 1H), 7.82 (dd, J=8.3, 0.6 Hz, 1H).

Workup

customNitrogen was bubbled through the reaction for 30 minutes
temperatureThe mixture was cooled to room temperature
filtrationfiltered
concentrationconcentrated in vacuo
customPurification via silica gel chromatography (Gradient: 0% to 30% diethyl ether in hexanes)

Sources & evidence

ORD record: ord-ed5c53a28e3040bb814ca6dcab3f1fff
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697673B2

Reaction notes

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