4-Fluorobenzoyl chloride → 4-Fluoro-N-(1-hydroxy-3-isobutyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-benzamide

HRID 60548Notes

Reaction equation

HRID 60548 reaction equation
[CH:1]1([CH:6]2[O:10][B:9]([OH:11])[C:8]3[CH:12]=[C:13]([NH:16]C(=O)C4C=CC=CC=4C(F)(F)F)[CH:14]=[CH:15][C:7]2=3)[CH2:5][CH2:4]CC1.[F:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1.[CH2:39]([Mg]Br)C(C)C>>[F:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:16][C:13]2[CH:14]=[CH:15][C:7]3[CH:6]([CH2:1][CH:5]([CH3:4])[CH3:39])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[O:35])=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 66927470N-(3-Cyclopentyl-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-2-trifluoromethyl-benzamideHCID 178418816HCID 178418816, compound

Product 1

HCID 673594844-Fluoro-N-(1-hydroxy-3-isobutyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-benzamide

Procedure

The title compound was prepared using a procedure similar to that of N-(3-cyclopentyl-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-2-trifluoromethyl-benzamide with 4-fluorobenzoyl chloride replacing 2-trifluoromethylbenzoyl chloride, and with isobutyl magnesium bromide replacing cyclopentyl magnesium bromide. Data: LCMS (M/Z): 328 (M+H); 1H NMR (DMSO-d6) δ: 10.25 (s, 1H), 9.11 (s, 1H), 8.07 (d, J=1.9 Hz, 1H), 7.98-8.04 (m, 2H), 7.71 (dd, J=8.2, 2.0 Hz, 1H), 7.29-7.37 (m, 3H), 5.11 (dd, J=9.8, 3.1 Hz, 1H), 1.81-1.93 (m, 1H), 1.65 (ddd, J=13.9, 9.0, 3.2 Hz, 1H), 1.27 (ddd, J=14.1, 9.7, 4.7 Hz, 1H), 0.98 (d, J=6.5 Hz, 3H), 0.89 (d, J=6.7 Hz, 3H).

Sources & evidence

ORD record
ord-27adea5c53f447b1b7234ca0713107c0
Source dataset
uspto-grants-2016_09
Patent number
US09440994B2

Reaction notes

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