2,2'-Bipyridine → HCID 131734992, compound

HRID 923493Notes

Reaction equation

HRID 923493 reaction equation
N1C=CC=CC=1[C:7]1[CH:12]=[CH:11]C=CN=1.ClC(Cl)C.[C:17]([Si:21]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[O:22][CH2:23][C:24]([NH:31][C:32]([C:34]1[N:38]2[CH:39]=[CH:40][CH:41]=[C:42]([O:43][CH2:44][C:45]3[C:50]([F:51])=[CH:49][CH:48]=[CH:47][C:46]=3[F:52])[C:37]2=[N:36][C:35]=1[CH3:53])=[O:33])([C:26]1[N:27]=[N:28][NH:29][N:30]=1)[CH3:25])([CH3:20])([CH3:19])[CH3:18].C1(B(O)O)CC1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[C:17]([Si:21]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)[O:22][CH2:23][C:24]([NH:31][C:32]([C:34]1[N:38]2[CH:39]=[CH:40][CH:41]=[C:42]([O:43][CH2:44][C:45]3[C:50]([F:51])=[CH:49][CH:48]=[CH:47][C:46]=3[F:52])[C:37]2=[N:36][C:35]=1[CH3:53])=[O:33])([C:26]1[N:27]=[N:28][N:29]([CH:11]2[CH2:12][CH2:7]2)[N:30]=1)[CH3:25])([CH3:18])([CH3:19])[CH3:20]

Participants

9

Reactant 6

HCID 14742,2'-BipyridineHCID 63651,1-Dichloroethane2×HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 2760897Cyclopropylboronic acidHCID 131734991HCID 131734991, compound

Product 1

HCID 131734992HCID 131734992, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 137 mg of copper (II) acetate, 121 mg of 2,2′-bipyridine, and 10 ml of dichloroethane was heated to an inner temperature of 70° C., and to this mixture was added a mixture of 501 mg of N-[1-{[tert-butyl (diphenyl)silyl]oxy}-2-(2H-tetrazol-5-yl)propan-2-yl]-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide, 135 mg of cyclopropylboronic acid, 182 mg of sodium carbonate, and 10 ml of dichloroethane, followed by stirring at 70° C. for 4 hours. The reaction mixture was left to be cooled to room temperature, and a saturated aqueous ammonium chloride solution and water were then added thereto. The aqueous layer was extracted with chloroform, and the organic layer was then combined and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 280 mg of N-[1-{[tert-butyl (diphenyl)silyl]oxy}-2-(2-cyclopropyl-2H-tetrazol-5-yl)propan-2-yl]-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. additionto this mixture was added
  2. waitThe reaction mixture was left
  3. temperatureto be cooled to room temperature
  4. extractionThe aqueous layer was extracted with chloroform
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-74e4c82efade4f998a4e15135b408ef7
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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