Potassium Carbonate → 2-{1-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrrolidin-3-yl}-N,N-dimethyl-acetamide

HRID 2234661노트

반응식

HRID 2234661 반응식
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2=[N:6][CH:7]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+].[CH3:41][N:42]([CH3:51])[C:43](=[O:50])[CH2:44][CH:45]1[CH2:49][CH2:48][NH:47][CH2:46]1>[Cu]I>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([N:47]3[CH2:48][CH2:49][CH:45]([CH2:44][C:43]([N:42]([CH3:41])[CH3:51])=[O:50])[CH2:46]3)[CH:3]=2)[N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:9]=1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 57731570N,N-dimethyl-2-pyrrolidin-3-yl-acetamideHCID 592970285-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 577316472-{1-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrrolidin-3-yl}-N,N-dimethyl-acetamide수율 30%

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

실험 절차

A microwave reaction vial was charged with 5-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (347 mg, 0.8 mmol), copper(I)-iodide (31 mg, 0.067 mmol), proline (37 mg, 0.13 mmol), potassium carbonate (332 mg, 1.6 mmol) and N,N-dimethyl-2-pyrrolidin-3-yl-acetamide (250 mg, 1.6 mmol) obtained from step 1. The vial was flushed with nitrogen and dimethylsulfoxide (2.0 ml) was added. The reaction tube was sealed irradiated in the microwave to 140° C. for 1 hour. The crude was partitioned between ethyl acetate (20 ml) and water (20 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (10 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (0% to 100% ethyl acetate in hexanes) to give 87 mg (30%) of 2-{1-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrrolidin-3-yl}-N,N-dimethyl-acetamide as a yellowish oil. MS: m/z 509.3 (M+H+).

후처리

  1. customA microwave reaction
  2. customThe vial was flushed with nitrogen and dimethylsulfoxide (2.0 ml)
  3. additionwas added
  4. customThe reaction tube was sealed
  5. customirradiated in the microwave to 140° C. for 1 hour
  6. customThe crude was partitioned between ethyl acetate (20 ml) and water (20 ml)
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with ethyl acetate (10 ml)
  9. dry with materialThe combined organic layers were dried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography on silica gel (0% to 100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-b3b8b12ffe724f959027d38058b20ccc
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709645B2

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