Dichloromethane → HCID 58381987, 화합물

HRID 1628022노트

반응식

HRID 1628022 반응식
[CH:1]1([N:7]2[C:11]3=[C:12]4[CH:18]=[CH:17][N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:13]4=[N:14][CH:15]=[C:10]3[NH:9][C:8]2=[O:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][S:29]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)(=[O:31])=[O:30].C(Cl)Cl.[NH4+].[OH-]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[CH:1]1([N:7]2[C:11]3=[C:12]4[CH:18]=[CH:17][N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])[C:13]4=[N:14][CH:15]=[C:10]3[N:9]([C:35]3[CH:36]=[CH:37][C:32]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:33][CH:34]=3)[C:8]2=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

7

반응물 4

HCID 6344Dichloromethane2회HCID 14923Ammonium HydroxideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 58382137HCID 58382137, 화합물

생성물 1

HCID 58381987HCID 58381987, 화합물수율 48.6%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 962Water용매

실험 절차

1-Cyclohexyl-6-((2-(trimethylsilyl)ethoxy)methyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (0.100 g, 0.259 mmol), 4-(methylsulfonyl)phenylboronic acid (0.103 g, 0.517 mmol, Acros), TEA (0.072 mL, 0.52 mmol) and 4 Å molecular sieves (130 mg) were added to DCM (2.6 mL) in a vial. Copper (II) acetate (0.047 g, 0.259 mmol) (Aldrich) was added in one portion and the vial was sealed. The mixture was stirred for about 22 h at rt. DCM (15 mL), water (5 mL), and concentrated NH4OH (5 mL) were added and the layers separated. The aqueous layer was extracted with DCM (5 mL). The combined organic layers were washed with water (10 mL), washed with brine (10 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (25 g Silicycle™ column) eluting with 10-50% EtOAc in DCM to give 1-cyclohexyl-3-(4-(methylsulfonyl)phenyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (0.068 g, 48%): LCMS (Table 2, Method b) Rt=3.16 min.; MS m/z: 541 (M+H)+.

후처리

  1. customthe vial was sealed
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with DCM (5 mL)
  4. washThe combined organic layers were washed with water (10 mL)
  5. washwashed with brine (10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (25 g Silicycle™ column)
  10. washeluting with 10-50% EtOAc in DCM

출처 및 근거

ORD 기록
ord-1dda845b3caf439791a149c30801dfc9
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785639B2

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