Lithium hydroxide, monohydrate → HCID 86715508, compound

HRID 2284596Notes

Reaction equation

HRID 2284596 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:15]=[CH:16][C:17]4[N:18]([C:20]([C:23]([O:25]CC)=[O:24])=[N:21][CH:22]=4)[CH:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:28].O[Li].O>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:15]=[CH:16][C:17]4[N:18]([C:20]([C:23]([OH:25])=[O:24])=[N:21][CH:22]=4)[CH:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:28]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86715509HCID 86715509, compound

Product 1

HCID 86715508HCID 86715508, compoundYield 77.2%

Reagents, catalysts & solvents 1

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

Procedure

Ethyl 6-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)imidazo[1,5-a]pyridine-3-carboxylate (2.1 g) and LiOH.H2O (400 mg) were stirred in THF/H2O (1:1, 60 mL) at 70° C. for 2 h. The reaction mixture was concentrated to dryness and diluted the pale yellow solid with water. The resulting semi-heterogeneous suspension was cooled in ice-bath, stirred and neutralized with aq. 3N HCl to pH 6. The solid aggregate was collected by filtration on Buchner funnel, washed with water and suction dried. Further processing the sample by drying over P2O5 in a vacuum desiccator provided the desired 6-(2-(4-Fluoro-3-methylphenyl)pyridin-3-yl)imidazo[1,5-a]pyridine-3-carboxylic acid (1.5 g, purity: 97%) as a pale yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additiondiluted the pale yellow solid with water
  3. temperatureThe resulting semi-heterogeneous suspension was cooled in ice-bath
  4. filtrationThe solid aggregate was collected by filtration on Buchner funnel
  5. washwashed with water and suction
  6. customdried
  7. dry with materialby drying over P2O5 in a vacuum desiccator

Sources & evidence

ORD record
ord-218d7d80bed44409aee190f4ba5e1527
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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