7-methylbenzo[c][1,2]oxaborole-1,5(3H)-diol → 5-Chloro-6-(1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-2-(4-oxopentyloxy)nicotinonitrile

HRID 2284518Notes

Reaction equation

HRID 2284518 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][C:5]([O:10][CH2:11][CH2:12][CH2:13][C:14](=[O:16])[CH3:15])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:18][C:19]1[C:24]2[B:25]([OH:28])[O:26][CH2:27][C:23]=2[CH:22]=[C:21]([OH:29])[CH:20]=1>>[Cl:1][C:2]1[C:3]([O:29][C:21]2[CH:20]=[C:19]([CH3:18])[C:24]3[B:25]([OH:28])[O:26][CH2:27][C:23]=3[CH:22]=2)=[N:4][C:5]([O:10][CH2:11][CH2:12][CH2:13][C:14](=[O:16])[CH3:15])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

3

Reactant 2

HCID 580798687-methylbenzo[c][1,2]oxaborole-1,5(3H)-diolHCID 866617215,6-Dichloro-2-(4-oxopentyloxy)nicotinonitrile

Product 1

HCID 667265405-Chloro-6-(1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-2-(4-oxopentyloxy)nicotinonitrile

Procedure

This compound was prepared from 5,6-dichloro-2-(4-oxopentyloxy)nicotinonitrile and 7-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) 1.67-1.71 (m, 2H), 2.02 (s, 3H), 2.33 (t, J=5.4 Hz, 2H), 2.44 (s, 3H), 4.01 (t, J=5.3 Hz, 2H), 4.95 (s, 2H), 7.0 (s, 1H), 7.07 (s, 1H), 8.56 (s, 1H), 9.0 (s, 1H).

Sources & evidence

ORD record
ord-78c9dd97cdf3466c9638060b0e859449
Source dataset
uspto-grants-2015_09
Patent number
US09145429B2

Reaction notes

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