Potassium Iodide → 4-[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2-ethyl-2,5,5-trimethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 2279119노트

반응식

HRID 2279119 반응식
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:9]=[C:10]([CH3:11])[C:5]2=[C:4]([CH2:18]OS(C)(=O)=O)[CH:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[NH:34][CH2:33][C:32]1([CH2:40][CH3:41])[CH3:39])=[O:30])([CH3:27])([CH3:26])[CH3:25].CCN(C(C)C)C(C)C.[I-].[K+]>C1COCC1.O>[C:24]([O:28][C:29]([N:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[N:34]([CH2:18][C:4]2[CH:3]=[C:2]([Br:1])[N:7]=[C:6]3[N:8]([CH:12]4[CH2:17][CH2:16][CH2:15][CH2:14][O:13]4)[N:9]=[C:10]([CH3:11])[C:5]=23)[CH2:33][C:32]1([CH2:40][CH3:41])[CH3:39])=[O:30])([CH3:27])([CH3:26])[CH3:25]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 900135322-Ethyl-2,5,5-trimethyl-piperazine-1-carboxylic acid tert-butyl esterHCID 90013581Methanesulfonic acid 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester

생성물 1

HCID 900134844-[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2-ethyl-2,5,5-trimethyl-piperazine-1-carboxylic acid tert-butyl ester수율 41.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
160 °C

실험 절차

A mixture of 130 mg of methanesulfonic acid 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester, 99 mg of 2-ethyl-2,5,5-trimethyl-piperazine-1-carboxylic acid tert-butyl ester, 0.11 ml of DIPEA and 5 mg of potassium iodide in 2 ml of dry THF was heated to 160° C. for 50 min in a microwave reactor. For workup the mixture was taken up in water and ethyl acetate, the phases were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtrated and concentrated in vacuo and the resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate). 75 mg (41%) of the title compound were obtained.

후처리

  1. customethyl acetate, the phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customthe resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-83e56100fdd74c8da199a1a6beb36591
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133181B2

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