Acetic Acid → HCID 178510075, compound

HRID 1255691Notes

Reaction equation

Br.C(O)(=O)C.[OH:6][B:7]1[C:11]2[CH:12]=[CH:13][C:14]([O:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([O:25]C)[N:18]=3)=[CH:15][C:10]=2[CH2:9][O:8]1>O>[OH:25][C:19]1[N:18]=[C:17]([O:16][C:14]2[CH:13]=[CH:12][C:11]3[B:7]([OH:6])[O:8][CH2:9][C:10]=3[CH:15]=2)[CH:24]=[CH:23][C:20]=1[C:21]#[N:22]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 48% HBr (2 mL) and acetic acid (4 mL) was added 6-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-2-methoxynicotinonitrile (D46) (0.300 mg, 1.06 mmol). The reaction was stirred for 24 hours at 50° C. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, and then filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column (7:3 to 9:1 ethyl acetate/hexane). The material was further purified by reverse phase HPLC to give 2-hydroxy-6-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)nicotinonitrile (0.027 g, 10% yield). ES(−)MS m/z=267 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ ppm 4.97 (s, 2H), 6.4 (br s, 1H), 7.15 (d, J=7.9 Hz, 1H), 7.25 (s, 1H), 7.77 (d, J=7.9 Hz, 1H), 8.09 (d, J=7.9 Hz, 1H), 9.24 (s, 1H), 12.7 (br s, 1H).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customThe solvent was removed under reduced pressure
customThe residue was purified by silica gel column (7:3 to 9:1 ethyl acetate/hexane)
customThe material was further purified by reverse phase HPLC

Sources & evidence

ORD record: ord-0b40e310ea9749749ea0f7985de43294
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461135B2

Reaction notes

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