Sodium Carbonate → 2-(benzyloxy)-5-(2-fluoropyridin-4-yl)-N-(pyridin-3-yl)benzamide

HRID 1623842Notes

Reaction equation

HRID 1623842 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:18]1[CH:19]=[CH:20][C:21]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:22]([CH:32]=1)[C:23]([NH:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)=[O:24]>O.COCCOC.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([C:18]2[CH:19]=[CH:20][C:21]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:22]([CH:32]=2)[C:23]([NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:24])[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27833962-Fluoropyridine-4-boronic acidHCID 369825032-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

Product 1

HCID 681079652-(benzyloxy)-5-(2-fluoropyridin-4-yl)-N-(pyridin-3-yl)benzamide

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-Fluoro-4-pyridinyl)boronic acid (425 mg, 3.02 mmol), bis(triphenylphosphine)palladium(II) chloride (70.6 mg, 0.10 mmol) and sodium carbonate (1066 mg, 10.06 mmol) as a solution in 2 ml of water was added to a solution of 5-bromo-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in example 2; 771 mg, 2.01 mmol) in 1,2-dimethoxyethane (20 ml). The mixture was heated to reflux for 2 hours. The mixture was diluted with ethyl acetate (50 ml) and water (50 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×50 ml). The organics were combined and evaporated. The residue was purified by chromatography on silica eluting with 0-10% methanol/dichloromethane 1% ammonia to yield the title compound as an off-white solid. 500 mg.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×50 ml)
  5. customevaporated
  6. customThe residue was purified by chromatography on silica eluting with 0-10% methanol/dichloromethane 1% ammonia

Sources & evidence

ORD record
ord-ac7f5f74a6e74cd1b2134c3c42bc7485
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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