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

HRID 1020839Notes

Reaction equation

HRID 1020839 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].[CH3:18][CH:19]1[O:23][B:22]([OH:24])[C:21]2[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:20]1=2>>[Cl:1][C:2]1[C:3]([O:29][C:27]2[CH:26]=[CH:25][C:21]3[B:22]([OH:24])[O:23][CH:19]([CH3:18])[C:20]=3[CH:28]=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 580800543-methylbenzo[c][1,2]oxaborole-1,5(3H)-diolHCID 866617205,6-Dichloro-2-(2-isopropoxyethoxy)nicotinonitrile

Product 1

HCID 667264875-Chloro-6-(1-hydroxy-3-methyl-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 3-methylbenzo[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), 1.40 (d, J=4.8 Hz, 3H), 3.4-3.47 (m, 3H), 4.07-4.1 (m, 2H), 5.2-5.22 (m, 1H), 7.23 (dd, J=6.0, 1.5 Hz, 1H), 7.36 (s, 1H), 7.75 (d, J=6.0 Hz, 1H), 8.59 (s, 1H), 9.18 (s, 1H).

Sources & evidence

ORD record
ord-d3d7b7b3bd4b43f8a0770fabd3bff28a
Source dataset
uspto-grants-2014_05
Patent number
US08716478B2

Reaction notes

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