Sodium Carbonate → HCID 46216224, compound

HRID 1880026Notes

Reaction equation

HRID 1880026 reaction equation
Br[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[NH:18][C:19]4[C:20]([N:25]=3)=[N:21][CH:22]=[CH:23][CH:24]=4)=[O:16])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)[C:3]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[NH:18][C:19]3[C:20]([N:25]=2)=[N:21][CH:22]=[CH:23][CH:24]=3)=[O:16])=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 59326825HCID 59326825, compound

Product 1

HCID 46216224HCID 46216224, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a round bottomed flask was added (4-(3-bromopyridin-2-yloxy)phenyl)(1H-imidazo[4,5-b]pyridin-2-yl)methanone (0.250 g, 0.633 mmol), pyridin-3-ylboronic acid (0.233 g, 1.898 mmol), PdCl2(dppf) (0.035 g, 0.063 mmol), and sodium carbonate (0.335 g, 3.16 mmol) in DMSO (1.581 mL) and Water (0.527 mL) at 80° C. to stir overnight. The reaction was worked up via seperatory funnel. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Synergi column, 4 micron, MAX-RP, 80 Å, 150×30 mM, 0.1% TFA in ACN/H2O, gradient 25% to 100% over 15 min to provide (4-(3,3′-bipyridin-2-yloxy)phenyl)(1H-imidazo[4,5-b]pyridin-2-yl)methanone. MS (ESI, pos. ion) m/z: 394.0 (M+1). IC50 (uM) +++++.

Workup

  1. customThe reaction was worked up via seperatory funnel
  2. customThe crude product was purified by reverse-phase preparative HPLC
  3. customover 15 min

Sources & evidence

ORD record
ord-1e7d06b479b74f29a49c7a55c6821c2d
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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