Dichloromethane → HCID 58381987、化合物

HRID 1628022ノート

反応式

HRID 1628022 の反応式
[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

参加物

7

反応物 4

HCID 6344Dichloromethane2 回HCID 14923Ammonium HydroxideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 58382137HCID 58382137、化合物

生成物 1

HCID 58381987HCID 58381987、化合物収率 48.6%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 962Water溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-1dda845b3caf439791a149c30801dfc9
出典データセット
uspto-grants-2014_07
特許番号
US08785639B2

反応ノート

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