Lithium Hydroxide → 6-(((Triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 570322Notes

Reaction equation

HRID 570322 reaction equation
[CH:1]([Si:4]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:13]([C:16]([O:18]CC)=[O:17])=[CH:14][N:15]=2)[CH:12]=1)([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1.CO.O>[CH:24]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:21]([CH3:23])[CH3:22])[O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:13]([C:16]([OH:18])=[O:17])=[CH:14][N:15]=2)[CH:12]=1)([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71281302Ethyl 6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 712813276-(((Triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The crude ethyl 6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylate (60) obtained above was dissolved in THF/MeOH/H2O (3:2:1, 5 mL). 6N LiOH (2.27 mL, 13.6 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. All solvents were removed and 6N HCl was added until pH 5-6. EtOAc (5 mL) was added and the mixture was stirred for 1 hour. The precipitate was filtered and dried to give 6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxylic acid (61). 1H NMR (400 MHz, d6-DMSO) δ 9.37 (s, 1H), 8.21 (s, 1H), 7.76 (dd, J=1.2, 9.2 Hz, 1H), 7.46 (dd, J=2.0, 9.2 Hz, 1H), 4.94 (s, 2H), 1.20 (m, 3H), 1.08 (d, J=6.8 Hz, 18H). MS m/z 349.2 (M+1)+.

Workup

  1. customAll solvents were removed
  2. addition6N HCl was added until pH 5-6
  3. additionEtOAc (5 mL) was added
  4. stirringthe mixture was stirred for 1 hour
  5. filtrationThe precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-14250d8eea4a4014a0e75529b040a03e
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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