Hydrochloric Acid → HCID 50907870, compound

HRID 2400289Notes

Reaction equation

HRID 2400289 reaction equation
[CH3:1][CH:2]([C:5]1[N:6]([CH2:17][C:18]2[N:23]=[C:22]([C:24]([O:26]C)=[O:25])[CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[C:9]([Cl:16])[CH:8]=2)[CH2:3][CH3:4].[OH-].[Na+].Cl.O>O1CCCC1.CO.C(OCC)(=O)C>[CH3:1][CH:2]([C:5]1[N:6]([CH2:17][C:18]2[N:23]=[C:22]([C:24]([OH:26])=[O:25])[CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[C:9]([Cl:16])[CH:8]=2)[CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67685028HCID 67685028, compound

Product 1

HCID 50907870HCID 50907870, compoundYield 98.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxylate (200 mg) in tetrahydrofuran (3.08 mL) and methanol (1.32 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.775 mL) at room temperature, followed by stirring for 2.5 hours. To the reaction mixture was added 1 mol/L hydrochloric acid (1.55 mL). To the mixture were added water and ethyl acetate to separate the organic layer. The organic layer was washed with water twice, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain the title compound (190 mg). 1H-NMR (DMSO-d6) δ ppm: 0.77 (3H, t, J=7.4 Hz), 1.17 (3H, d, J=6.9 Hz), 1.40-1.70 (2H, m), 2.80-2.95 (1H, m), 3.83 (3H, s), 5.45-5.65 (2H, m), 6.30 (1H, s), 6.70 (1H, d, J=7.3 Hz), 7.20 (1H, s), 7.55 (1H, s), 7.80-7.95 (2H, m), 13.00-13.50 (1H, br).

Workup

  1. customto separate the organic layer
  2. washThe organic layer was washed with water twice
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-51780719cc14420aaa9b7b3b43e584c0
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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