Sodium Carbonate → HCID 57502604, compound

HRID 655932Notes

Reaction equation

HRID 655932 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]=[C:15]3[C:10]([C:11]([C:18]([NH2:20])=[O:19])=[CH:12][C:13]([F:17])=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=1.C([O-])([O-])=O.[Na+].[Na+].F[B-](F)(F)F>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)Cl>[F:17][C:13]1[CH:12]=[C:11]([C:18]([NH2:20])=[O:19])[C:10]2[C:15](=[CH:16][N:8]([C:5]3[CH:6]=[CH:7][C:2]([C:23]4[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=4)=[CH:3][CH:4]=3)[N:9]=2)[CH:14]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 26255TetrafluoroborateHCID 27343783-Pyridinylboronic acidHCID 57425159HCID 57425159, compound

Product 1

HCID 57502604HCID 57502604, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (D3) (1.0 eq) and pyridine-3-boronic acid (1.3 eq) in DMF (1.0 M) together with 2N Na2CO3 solution (2.0 eq) was degassed with a stream of Ar for 30 min. tBu3PH+BF4− (0.05 eq) and Pd2(dba)3 (0.05 eq) were added and the reaction mixture was heated at 90° for 48 h. The mixture was cooled to RT, DCM was added and the organic phase was washed with sat. aq. NaHCO3 solution, brine, dried (Na2SO4). The solution was concentrated under reduced pressure and the residue was purified by chromatography on silica gel eluting with 50-90% EtOAc/Petroleum ether then 10% MeOH/DCM to obtain the title compound as a yellow powder. 1H NMR (400 MHz, DMSO-d6, 300K) δ 9.40 (1H, s), 9.01 (1H, d, J=1.6 Hz), 8.63 (1H, dd, J=4.8, 1.6 Hz), 8.57 (1H, br. s), 8.32 (2H, d, J=8.8 Hz), 8.20 (1H, d, J=7.8 Hz), 8.10 (1H, br. s), 8.01 (2H, d, J=8.8 Hz), 7.88-7.82 (2H, m), 7.54 (1H, dd, J=7.8, 4.8 Hz). MS (ES) C19H13FN4O requires: 332. Found: 333 (M+H+).

Workup

  1. additionwere added
  2. temperaturethe reaction mixture was heated at 90° for 48 h
  3. washthe organic phase was washed with sat. aq. NaHCO3 solution, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationThe solution was concentrated under reduced pressure
  6. customthe residue was purified by chromatography on silica gel eluting with 50-90% EtOAc/Petroleum ether

Sources & evidence

ORD record
ord-c911f0c466374ae8b8baffd23a197bfd
Source dataset
uspto-grants-2011_12
Patent number
US08071623B2

Reaction notes

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