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

HRID 1883133노트

반응식

HRID 1883133 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-380412ca0fb64fbca718e02ebf8db516
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759428B2

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