Lithium hydroxide, monohydrate → HCID 59830345, compound
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][C:11]([CH:19]([CH3:21])[CH3:20])=[N:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].O.[OH-].[Li+]>>[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([CH:19]([CH3:21])[CH3:20])=[N:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2]Participants
Procedure
3-Cyanophenylboronic acid (0.4 g, 2.74 mmol), was reacted with Example B38 (0.5 g, 2.74 mmol) in the presence of copper (II) acetate (0.5 g, 2.74 mmol) at 80° C. for 3 hours in pyridine (3.5 ml) to provide ethyl 1-(3-cyanophenyl)-3-isopropyl-1H-pyrazole-5-carboxylate (0.18 g, 24% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.06 (m, 1H), 7.92 (m, 1H), 7.83 (m, 1H), 7.69 (m, 1H), 7.02 (s, 1H), 4.20 (q, J=6 Hz, 1H), 3.00 (m, 1H), 1.26 (d, J=6 Hz, 6H), 1.20 (t, J=6 Hz, 3H); MS (ESI) m/z: 284.2 (M+H+). Hydrolysis of the ester with lithium hydroxide monohydrate provided 1-(3-cyanophenyl)-3-isopropyl-1H-pyrazole-5-carboxylic acid in 94% yield. 1H NMR (400 MHz, DMSO-d6): δ 8.02 (m, 1H), 7.89 (m, 1H), 7.83 (m, 1H), 7.67 (m, 1H), 6.97 (s, 1H), 3.00 (m, 1H), 1.26 (q, J=6 Hz, 6H); MS (ESI) m/z: 256.0 (M+H+).
Sources & evidence
- ORD record
- ord-22c6fcc444ef4c02b855469e7aeca612
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188113B2
Reaction notes
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