Cesium carbonate → HCID 178461217, compound

HRID 81100Notes

Reaction equation

HRID 81100 reaction equation
Cl[C:2]1[C:7]2[N:8]([CH2:23][C@H:24]3[CH2:29][CH2:28][C@H:27]([CH3:30])[CH2:26][CH2:25]3)[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][C@H:12]3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][C:6]=2[CH:5]=[C:4]([Cl:31])[N:3]=1.[Cl:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[N:37][CH:38]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:31][C:4]1[N:3]=[C:2]([C:35]2[CH:36]=[N:37][CH:38]=[C:33]([Cl:32])[CH:34]=2)[C:7]2[N:8]([CH2:23][C@H:24]3[CH2:25][CH2:26][C@H:27]([CH3:30])[CH2:28][CH2:29]3)[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][C@H:12]3[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[N:10][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 201118775-Chloropyridine-3-boronic acidHCID 178461219HCID 178461219, compound

Product 1

HCID 178461217HCID 178461217, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
90 °C

Procedure

4,6-dichloro-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine (3.44 g, 7.49 mmol), 5-chloropyridine-3-boronic acid (1.32 g, 08.39 mmol), cesium carbonate (12.2 g, 37.4 mmol), and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride (1.1 g, 1.49 mmol) were combined in a vial that had been oven-dried and flushed with nitrogen. Dioxane (75 mL) was added, and the vial was sealed and heated to 90° C. for 4 hours. The reaction mixture was cooled to room temperature, filtered over celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient) to afford 6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine. MS ESI calc'd. for C29H31Cl2N5O [M+H]+ 536. found 536.

Workup

  1. customhad been oven-dried
  2. customflushed with nitrogen
  3. additionDioxane (75 mL) was added
  4. customthe vial was sealed
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationfiltered over celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-125b16412a86458ba63b0c3dbfd6c73f
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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