Sodium Hydroxide → HCID 63749119, compound

HRID 2170605Notes

Reaction equation

HRID 2170605 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16]C)=[O:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([OH:16])=[O:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71075467HCID 71075467, compound

Product 1

HCID 63749119HCID 63749119, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 1-(2,4-difluorobenzyl)-1H-indole-5-carboxylate (3.14 g, 10.4 mmol, 1 equiv) in methanol (50 mL) was added a 5 N NaOH solution (50 mL, 104 mmol, 10 equiv). The reaction mixture was stirred 2 h at 40° C. The mixture was then acidified and extracted with DCM. After concentration in vacuo, the title compound was precipitated in Et2O to afford a white powder (2.82 g, 9.8 mmol, 96%). ESI-MS (m/z): 288 [M+H]+.

Workup

  1. extractionextracted with DCM
  2. concentrationAfter concentration in vacuo
  3. customthe title compound was precipitated in Et2O

Sources & evidence

ORD record
ord-01540a06029246d697a748a9e32d38d8
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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