Ethanol → HCID 71212115, compound

HRID 513211Notes

Reaction equation

HRID 513211 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[CH:12][CH:13]=[C:14]3[C:18]([CH2:19][CH2:20][O:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=4)=[C:17]([C:33]([O:35]CC)=[O:34])[NH:16][C:15]=23)[CH:7]=[CH:8][CH:9]=1)[CH3:2].CCO.O.[Li+].[OH-]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[CH:12][CH:13]=[C:14]3[C:18]([CH2:19][CH2:20][O:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]([F:30])([F:31])[F:32])=[CH:24][CH:23]=4)=[C:17]([C:33]([OH:35])=[O:34])[NH:16][C:15]=23)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 71212594HCID 71212594, compound

Product 1

HCID 71212115HCID 71212115, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-(3-ethoxyphenyl)-3-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (80 mg, 0.15 mmol) in THF (2 mL) was added EtOH (0.4 mL)m and water (0.4 mL). Solid LiOH (75 mg, 3.1 mmol) was then added in a single portion. After 2 h at r.t. and 2 h at 50 C, the reaction was quenched with 5% potassium bisulfate until acidic (˜pH 3) which caused a white precipitate to form. This was filtered and washed with water to yield the title compound (65 mg). HRMS (ESI) calc (M+H)+=487.1475. found 487.1478.

Workup

  1. custom2 h at 50 C, the reaction was quenched with 5% potassium bisulfate until acidic (˜pH 3) which
  2. customto form
  3. filtrationThis was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-ea0ef8634e354d1bad271cd028e0e252
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

Loading…