6-Fluorobenzo[c][1,2]oxaborole-1,5(3H)-diol → 5-Chloro-6-(6-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-2-(2-isopropoxyethoxy)nicotinonitrile

HRID 1020837Notes

Reaction equation

HRID 1020837 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][C:5]([O:10][CH2:11][CH2:12][O:13][CH:14]([CH3:16])[CH3:15])=[C:6]([CH:9]=1)[C:7]#[N:8].[F:18][C:19]1[C:20]([OH:29])=[CH:21][C:22]2[CH2:26][O:25][B:24]([OH:27])[C:23]=2[CH:28]=1>>[Cl:1][C:2]1[C:3]([O:29][C:20]2[C:19]([F:18])=[CH:28][C:23]3[B:24]([OH:27])[O:25][CH2:26][C:22]=3[CH:21]=2)=[N:4][C:5]([O:10][CH2:11][CH2:12][O:13][CH:14]([CH3:16])[CH3:15])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

3

Reactant 2

HCID 580799216-Fluorobenzo[c][1,2]oxaborole-1,5(3H)-diolHCID 866617205,6-Dichloro-2-(2-isopropoxyethoxy)nicotinonitrile

Product 1

HCID 667265505-Chloro-6-(6-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-2-(2-isopropoxyethoxy)nicotinonitrile

Procedure

This compound was prepared from 5,6-dichloro-2-(2-isopropoxyethoxy)nicotinonitrile and 6-fluorobenzo[c][1,2]oxaborole-1,5(3H)-diol in a similar manner to that of D230. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 1.0 (d, J=4.5 Hz, 6H), 3.32-3.45 (m, 3H), 4.04-4.05 (m, 2H), 5.0 (s, 2H), 7.53 (d, J=4.8 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 8.63 (s, 1H), 9.4 (s, 1H).

Sources & evidence

ORD record
ord-8963c290e1104df796e8b6fc72c85c09
Source dataset
uspto-grants-2014_05
Patent number
US08716478B2

Reaction notes

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