Lithium Hydroxide → HCID 118590385, compound

HRID 1054438Notes

Reaction equation

HRID 1054438 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([C:23]([O:25]CC)=[O:24])=[CH:21][N:22]=2)[CH:19]=1.[Li+].[OH-]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118595411HCID 118595411, compound

Product 1

HCID 118590385HCID 118590385, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To stirred solution of (R)-ethyl 6-(2-(2,5-difluorophenyl)pyrrolidin 1-yl)imidazo[1,2-a]pyridine-3-carboxylate (4.5 g, 12.12 mmol) in Ethanol was added 1M LiOH (0.87 g, 36.3 mmol) solution and stirred for 5 h at 85° C. Solvent was removed under reduced pressure and residue was dissolved in water, extracted unwanted impurities with Diethyl ether and water layer was acidified with 2N HCl and solid was collected by filtration. Solid was dried under high vacuum to afford (R)-6-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylic acid (Int-14) as pale yellow solid (3.5 g, 84.1% yield), MS (ESI): m/z 344.2 (M+H).

Workup

  1. customSolvent was removed under reduced pressure and residue
  2. dissolutionwas dissolved in water
  3. extractionextracted unwanted impurities with Diethyl ether and water layer
  4. filtrationwas collected by filtration
  5. customSolid was dried under high vacuum

Sources & evidence

ORD record
ord-bd990c09c0664599b5b29edf540bfa30
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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