Skatole → (6-Chloropyrimidin-4-yl)-(3-methylindol-1-yl)-methanone

HRID 74526

반응식

HRID 74526 반응식
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[Cl:13][C:14]1[N:19]=[CH:18][N:17]=[C:16]([C:20](Cl)=[O:21])[CH:15]=1.CCOC(C)=O>C1COCC1>[Cl:13][C:14]1[N:19]=[CH:18][N:17]=[C:16]([C:20]([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([CH3:3])=[CH:5]2)=[O:21])[CH:15]=1

참가 물질

6

반응물 4

HCID 6736SkatoleHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 184220986-Chloropyrimidine-4-carbonyl chloride

생성물 1

HCID 58386489(6-Chloropyrimidin-4-yl)-(3-methylindol-1-yl)-methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under a nitrogen atmosphere 120 mg (3.00 mmol) sodium hydride (60% in mineral oil) were added batchwise to 380 mg (2.90 mmol) 3-methylindole in 15 mL THF and the mixture was stirred for 30 min at RT. 500 mg (2.83 mmol) 6-chloropyrimidine-4-carboxylic acid chloride were added batchwise and then the reaction mixture was stirred for 2 h at RT. Then 50 mL EtOAc were added and the mixture was washed with 50 mL saturated sodium hydrogen carbonate solution (1×), 30 mL water and with 50 mL 1 M hydrochloric acid. The organic phase was dried on sodium sulphate, filtered and then evaporated down i. vac. The product was used in the next step without further purification.

후처리

  1. stirringthe reaction mixture was stirred for 2 h at RT
  2. washthe mixture was washed with 50 mL saturated sodium hydrogen carbonate solution (1×), 30 mL water and with 50 mL 1 M hydrochloric acid
  3. customThe organic phase was dried on sodium sulphate
  4. filtrationfiltered
  5. customevaporated down i
  6. customThe product was used in the next step without further purification

출처 및 근거

ORD 기록
ord-d1f7ccbf2f7d40a5bcc870d4b8890987
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829006B2

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