Potassium Carbonate → HCID 66672822, compound

HRID 422083Notes

Reaction equation

HRID 422083 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:19]=[CH:18][C:17]4[O:20][C:21](Br)=[CH:22][C:16]=4[C:15]3=[O:24])=[CH:11][CH:12]=2)[CH:7]=[N:6]1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:19]=[CH:18][C:17]4[O:20][C:21]([C:30]5[CH:31]=[CH:32][C:27]([Cl:26])=[CH:28][CH:29]=5)=[CH:22][C:16]=4[C:15]3=[O:24])=[CH:11][CH:12]=2)[CH:7]=[N:6]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 58015564HCID 58015564, compound

Product 1

HCID 66672822HCID 66672822, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl-2(5-(2-bromo-4-oxofuro[3,2-c]pyridine-5(4H)-yl)1H-indazol-1-yl)acetate (0.77 g, 19 mmol) in DMSO (44 mL) was added 4-chlorophenyl boronic acid (0.32 g, 2.1 mmol), K2CO3 (0.52 g, 3.8 mmol) and bis(triphenylphosphine)palladium (II) chloride (0.13 g, 0.19 mmol). The solution was evacuated for 15 minutes under high vacuum then backfilled with argon. The process was repeated three times. The reaction mixture was stirred at 90° C. for 2 h; then the reaction mixture was diluted with H2O (20 mL) and extracted with CH2Cl2 (3×40 mL). The extracts were washed with brine (2×50 mL), dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (silica gel, CH2Cl2/MTBE, 100:0 to 1:1) yielded the title compound (0.38 mg, 46%) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.12 (s, 1H), 7.77-7.63 (m, 4H), 7.53-7.41 (m, 4H), 7.35 (d, J=7.5 Hz, 1H), 6.68 (dd, J=7.5, 0.9 Hz, 1H), 5.22 (s, 2H), 3.78 (s, 3H); ESI MS m/z 434 [M+H]+.

Workup

  1. customThe solution was evacuated for 15 minutes under high vacuum
  2. additionthen the reaction mixture was diluted with H2O (20 mL)
  3. extractionextracted with CH2Cl2 (3×40 mL)
  4. washThe extracts were washed with brine (2×50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (silica gel, CH2Cl2/MTBE, 100:0 to 1:1)

Sources & evidence

ORD record
ord-10734ac901194314b059f517fa68e45d
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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