7-fluorobenzo[c][1,2]oxaborole-1,5(3H)-diol → 6-(7-Fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-2-(2-isopropoxyethoxy)-4-(trifluoromethyl)nicotinonitrile

HRID 2284523Notes

Reaction equation

HRID 2284523 reaction equation
Cl[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:5]([C:6]#[N:7])=[C:4]([O:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])[N:3]=1.[F:21][C:22]1[C:27]2[B:28]([OH:31])[O:29][CH2:30][C:26]=2[CH:25]=[C:24]([OH:32])[CH:23]=1>>[F:21][C:22]1[C:27]2[B:28]([OH:31])[O:29][CH2:30][C:26]=2[CH:25]=[C:24]([O:32][C:2]2[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:5]([C:6]#[N:7])=[C:4]([O:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])[N:3]=2)[CH:23]=1

Participants

3

Reactant 2

HCID 580799197-fluorobenzo[c][1,2]oxaborole-1,5(3H)-diolHCID 866617356-Chloro-2-(2-isopropoxyethoxy)-4-(trifluoromethyl)nicotinonitrile

Product 1

HCID 667264756-(7-Fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-2-(2-isopropoxyethoxy)-4-(trifluoromethyl)nicotinonitrile

Procedure

This compound was prepared from 6-chloro-2-(2-isopropoxyethoxy)-4-(trifluoromethyl)nicotinonitrile and 7-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) 1.06 (d, J=6 Hz, 6H), 3.52-3.55 (m, 1H), 3.59-3.61 (t, J=4.8 Hz, 2H), 4.26-4.28 (t, J=4.8 Hz, 2H), 5.07 (s, 2H), 7.18 (d, J=8.0 Hz, 1H), 7.27 (s, 1H), 7.38 (s, 1H), 9.39 (s, 1H).

Sources & evidence

ORD record
ord-ab61e2c43ade4d76812ba9f8b96755d0
Source dataset
uspto-grants-2015_09
Patent number
US09145429B2

Reaction notes

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