Dichloromethane → HCID 58381987, compound

HRID 1628022Notes

Reaction equation

HRID 1628022 reaction equation
[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

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 14923Ammonium HydroxideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 58382137HCID 58382137, compound

Product 1

HCID 58381987HCID 58381987, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-1dda845b3caf439791a149c30801dfc9
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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