Lithium Hydroxide → 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylic acid

HRID 1529442Notes

Reaction equation

HRID 1529442 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13]C)=[O:12])[CH:9]=2)[N:4]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:3]=1.[Li+].[OH-]>C1COCC1.CO>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[N:4]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67959982methyl 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate

Product 1

HCID 679598343-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate ((5.0 g, 12.9 mmol) in THF: MeOH (70:30) (50 mL) was added LiOH (3.10 g, 129.0 mmol) in one lot and the reaction was stirred at RT for 12 h. The solvent were removed in vacuo and the residue was diluted with water and quenched with 1N HCl (50 mL) to obtain off white precipitate. The suspension was stirred for 10 min and filtered and dried to give 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylic acid (4.2 g, 87%) as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.09 (s, 1H), 8.03-8.06 (m, 2H), 7.84-7.86 (m, 1H), 5.93 (dd, 1 H, J=9.7, 2.3 Hz), 3.90 (d, 1 H, J=11.9 Hz), 3.74-3.76 (m, 1H), 2.35-2.41 (m, 1H), 1.97-2.00 (m, 2H), 1.69-1.80 (m, 1H), 1.41-1.58 (m, 2H).

Workup

  1. customThe solvent were removed in vacuo
  2. additionthe residue was diluted with water
  3. customquenched with 1N HCl (50 mL)
  4. customto obtain off white precipitate
  5. stirringThe suspension was stirred for 10 min
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-b9684e8207124513840230ef6a787be4
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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