Lithium Hydroxide → HCID 86715495, compound

HRID 2284587Notes

Reaction equation

HRID 2284587 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:15]=[C:16]4[C:20](=[C:21]([C:23]([O:25]C)=[O:24])[CH:22]=3)[NH:19][N:18]=[CH:17]4)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:27].[Li+].[OH-]>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:15]=[C:16]4[C:20](=[C:21]([C:23]([OH:25])=[O:24])[CH:22]=3)[NH:19][N:18]=[CH:17]4)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:27]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86715493HCID 86715493, compound

Product 1

HCID 86715495HCID 86715495, compoundYield 115.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 5-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)-1H-indazole-7-carboxylate (300 mg, 0.55 mmol) was saponified by LiOH (0.12 g,) in THF/H2O (1:1, 8 mL) for 2 days. The reaction mixture was concentrated to dryness, diluted with water (4 mL) and neutralized by the addition of aq. 2N HCl. The solid formed after the neutralization was filtered and suction dried to obtain the title compound as a white solid (220 mg). 1H NMR (DMSO-d6): δ 13.15 (s, 1H),8.67 (app dd, 1H, J=1.4 and 4.7 Hz), 8.17 (s, 1H), 7.97-7.92 (m, 2H), 7.68 (d, 1H, J=1.7 Hz), 7.51 (dd, 1H, J=4.7 and 7.6 Hz), 7.38 (d, 1H, 7.6 Hz), 6.93-6.90 (m, 2H), 2.12 (s, 3H).19F NMR (DMSO-d6): δ −118.43 (s).LCMS: 97%, MS (m/e) 348 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additiondiluted with water (4 mL)
  3. additionneutralized by the addition of aq. 2N HCl
  4. customThe solid formed after the neutralization
  5. filtrationwas filtered
  6. customsuction dried

Sources & evidence

ORD record
ord-6c3e436b1f424280855639a3dc420851
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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