Methyl chloroacetate → 7-tert-Butyl 1-methyl 3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylate

HRID 221478ノート

反応式

HRID 221478 の反応式
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]2[C:20]([C:24]([F:27])([F:26])[F:25])=[N:21][C:22](Br)=[C:16]2[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].ClC[C:30]([O:32][CH3:33])=[O:31]>CO.[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2]>[CH3:33][O:32][C:30]([C:22]1[N:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:17]2[CH2:18][CH2:19][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:15][C:16]=12)=[O:31]

参加物

6

反応物 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 57518451tert-butyl 1-bromo-3-(trifluoromethyl)-5H,6H,7H,8H-imidazo(1,5-a)pyrazine-7-carboxylate

生成物 1

HCID 575184527-tert-Butyl 1-methyl 3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylate収率 67.8%

試薬・触媒・溶媒 2

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)触媒HCID 887Methanol溶媒

実験手順

Octacarbonyldicobalt (5.54 g, 16.2 mmol) and potassium carbonate (11.2 g, 81.1 mmol) was dissolved in 100 mL of methanol under stirring. The reaction mixture was stirred for 15 minutes at 60° C., and 1-bromo-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester 27b (3 g, 8.11 mmol) and methyl chloroacetate (5.25 g, 48.6 mmol) were then added to the solution. The reaction mixture was reacted for 6 hours under a carbon monoxide atmosphere and monitored by thin layer chromatography until the disappearance of the starting materials. After cooling to room temperature, the reaction mixture was filtered through a pad of silica gel, rinsed with methanol. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylic acid 7-tert-butyl ester 1-methyl ester 27c (1.92 g, yield 67%) as a white solid. (Reference: J. Organomet. Chem, 1985, 293)

後処理

  1. stirringThe reaction mixture was stirred for 15 minutes at 60° C.
  2. customThe reaction mixture was reacted for 6 hours under a carbon monoxide atmosphere
  3. filtrationthe reaction mixture was filtered through a pad of silica gel
  4. washrinsed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d14ccd8083c348e4b44b3ecc9a3d721c
出典データセット
uspto-grants-2012_06
特許番号
US08207161B2

反応ノート

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