Lithium Hydroxide → Methyl 6-bromo-1-methyl-1H-indole-2-carboxylate

HRID 1883133Notes

Reaction equation

HRID 1883133 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([Br:15])[CH:9]=2)=[O:5])C.[Li+].[OH-].[CH3:18]O.O>>[CH3:1][O:3][C:4]([C:6]1[N:7]([CH3:18])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([Br:15])[CH:9]=2)=[O:5]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 70094966-Bromo-1H-indole-2-carboxylic acid ethyl esterHCID 22242641Methanol--water (1/1)

Product 1

HCID 4777911Methyl 6-bromo-1-methyl-1H-indole-2-carboxylate

Procedure

6-Bromo-1-methyl-1H-indole-2-carboxylic acid methyl ester was prepared by N-methylation of 6-bromo-1H-indole-2-carboxylic acid ethyl ester using the procedure described in Example 13 for N-methylation of indole carboxylic acid esters. Ester hydrolysis was performed with LiOH (4 equ.) in methanol-water 4:1, 12 h at room temperature. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was acidified to pH˜2-3 with 2N HCl and extracted in ethyl acetate. The organic phase was washed with brine, dried (Na2SO4) and evaporated in vacuo to yield 95% of 6-bromo-1-methyl-1H-indole-2-carboxylic acid [(1S,2R)-2-cyanomethyl-carbamoyl)-cyclohexyl]-amide; m/z 253.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionextracted in ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-380412ca0fb64fbca718e02ebf8db516
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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