Boron tribromide → HCID 67509250, compound

HRID 2172876Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH2:18][O:19]C)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.B(Br)(Br)Br>C(=O)(O)[O-]>[Cl:1][C:2]1[C:3]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH2:18][OH:19])(=[O:16])=[O:15])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled −78° C. solution of 3-chloro-6-(4-((2-methoxyethyl)sulfonyl)piperazin-1-yl)-2,2′-bipyridine (134 mg, 0.338 mL) in (2 mL), boron tribromide (0.139 mL, 0.737 mmol) was added. After 1 h, the reaction mixture was warmed to 0° C. and stirred for an additional 1 h. Saturated aqueous bicarbonate (10 mL) was added and extracted with CH2Cl2 (2×10 mL). The combined organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure and purified by column chromatography (60 to 100% ethyl acetate/heptane) to obtain pure product (87 mg, 67% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.65 (d, J=4.80 Hz, 1 H) 7.92 (td, J=7.71, 1.77 Hz, 1 H) 7.75 (d, J=9.09 Hz, 1 H) 7.69 (d, J=7.83 Hz, 1 H) 7.44 (td, J=6.19, 1.01 Hz, 1 H) 6.99 (d, J=8.84 Hz, 1 H) 5.02 (t, J=5.43 Hz, 1 H) 3.75 (q, J=6.06 Hz, 2 H) 3.59-3.67 (m, 4 H) 3.24-3.30 (m, 4 H) 3.21 (t, J=6.19 Hz, 2 H). LCMS (M+H)+: 383.0.

Workup

extractionextracted with CH2Cl2 (2×10 mL)
washThe combined organic layer was washed with brine (10 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
custompurified by column chromatography (60 to 100% ethyl acetate/heptane)

Sources & evidence

ORD record: ord-14b636aef5c84821b67ac6c5140a9ea6
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056865B2

Reaction notes

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