Sodium Carbonate → 6-(1-triphenylmethyl-1H-imidazol-4-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 1878447Notes

Reaction equation

HRID 1878447 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15](B4OC(C)(C)C(C)(C)O4)=[CH:14][N:13]3[CH:27]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].I[C:35]1[N:36]=[CH:37][N:38]([C:40]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:39]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>[C:53]1([C:40]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:38]2[CH:39]=[C:35]([C:15]3[CH:16]=[CH:17][C:12]4[N:13]([CH:27]=[C:10]([C:8]([NH:7][C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[O:9])[N:11]=4)[CH:14]=3)[N:36]=[CH:37]2)[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6182524-Iodo-1-tritylimidazoleHCID 44135943N-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxamide2×

Product 1

HCID 687815006-(1-triphenylmethyl-1H-imidazol-4-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamideYield 42.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

540 mg of N-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxamide (Intermediate 5), 13 mL of dioxane, 6.8 mL of 2M sodium carbonate solution, 843 mg of 4-iodo-1-triphenylmethylimidazole and 86 mg of tetrakis(triphenylphosphine)-palladium are placed in a microwave tube. The mixture is heated for 10 minutes in a microwave machine set at 120° C., and then cooled and concentrated under reduced pressure. The residue is taken up in 100 mL of dichloromethane. After washing with water, the organic phase is dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue is chromatographed on a silica cartridge, eluting with a gradient of cyclohexane and ethyl acetate (from 100/0 to 60/40). The fractions containing the expected product are combined and concentrated to dryness under reduced pressure. The solid is crystallized from acetonitrile. The crystals are washed with acetonitrile and then with ethyl ether and then dried under vacuum to give 342 mg of 6-(1-triphenylmethyl-1H-imidazol-4-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. temperatureThe mixture is heated for 10 minutes in a microwave machine
  2. customset at 120° C.
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. washAfter washing with water
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue is chromatographed on a silica cartridge
  9. washeluting with a gradient of cyclohexane and ethyl acetate (from 100/0 to 60/40)
  10. additionThe fractions containing the expected product
  11. concentrationconcentrated to dryness under reduced pressure
  12. customThe solid is crystallized from acetonitrile
  13. washThe crystals are washed with acetonitrile
  14. dry with materialwith ethyl ether and then dried under vacuum

Sources & evidence

ORD record
ord-0299c2c178bd4576ba3652f5cec20a0b
Source dataset
uspto-grants-2012_11
Patent number
US08314109B2

Reaction notes

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