Lithium Hydroxide → (r/s)-5-Imidazo[4,5-b]pyridine-3-yl-3-oxo-indan-1-carboxylic acid

HRID 1660986Notes

Reaction equation

HRID 1660986 reaction equation
C([O:3][C:4]([CH:6]1[C:14]2[C:9](=[CH:10][C:11]([N:15]3[C:19]4=[N:20][CH:21]=[CH:22][CH:23]=[C:18]4[N:17]=[CH:16]3)=[CH:12][CH:13]=2)[C:8](=[O:24])[CH2:7]1)=[O:5])C.[Li+].[OH-]>C1COCC1>[N:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[N:15]([C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[CH:6]([C:4]([OH:5])=[O:3])[CH2:7][C:8]3=[O:24])[CH:16]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67021616HCID 67021616, compound

Product 1

HCID 67021572(r/s)-5-Imidazo[4,5-b]pyridine-3-yl-3-oxo-indan-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-imidazo[4,5-b]pyridine-3-yl-3-oxo-indan-1-carboxylic acid ethyl ester (297 mg, 0.924 mmol) and 1N LiOH (1 mL, 1 mmol) in THF (1.7 mL) is stirred at rt for 15 min. THF is removed in vacuo, the residue taken up in EtOAC and washed with 1N LiOH. The aqueous layer was acidified with 1M HCl and extracted with EtOAc. The organic layer was washed with brine, dried with MgSO4, filtered and concentrated. (R/S)-5-Imidazo[4,5-b]pyridine-3-yl-3-oxo-indan-1-carboxylic acid is obtained as a brown solid. Title compound: 1H NMR (DMSO-d6): 9.0 (s, 1H), 8.5 (d, 1H), 8.4 (d, 1H), 8.3 (s, 1H), 8.2 (d, 1H) 7.9 (d, 1H), 7.4 (dd, 1H) 4.4 (m, 1H), 3.0 (m, 2H); tR=0.9 min (System 2).

Workup

  1. customTHF is removed in vacuo
  2. washwashed with 1N LiOH
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e33d9e08c8a451b96a5ab69d370af91
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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