Hydrochloric Acid → 3-(Benzo[d][1,3]dioxol-5-yl)-2-phenylquinoxaline-6-carboxylic acid

HRID 2205111Notes

Reaction equation

HRID 2205111 reaction equation
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=2.[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[C:30](B(O)O)[C:25]=2[O:24][CH2:23]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Cl>O1CCOCC1.O.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]>[O:22]1[C:26]2[CH:27]=[CH:28][C:29]([C:2]3[C:3]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[N:4][C:5]4[C:10]([N:11]=3)=[CH:9][C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=4)=[CH:30][C:25]=2[O:24][CH2:23]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 41926592,3-Methylenedioxyphenyl boronic acidHCID 86667202HCID 86667202, compound

Product 1

HCID 867181103-(Benzo[d][1,3]dioxol-5-yl)-2-phenylquinoxaline-6-carboxylic acidYield 41.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A suspension of methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (80 mg, 0.23 mmol, 1.00 equiv), benzo[d][1,3]dioxol-4-ylboronic acid (59 mg, 0.36 mmol, 1.50 equiv), tricyclohexylphosphine (9 mg, 0.03 mmol, 0.14 equiv), Pd2(dba)3 (13 mg, 0.01 mmol, 0.06 equiv), and K3PO4 (149 mg, 0.80 mmol, 3.00 equiv). in dioxane/H2O (1/0.5 mL) in a 10-mL sealed tube was allowed to react, with stifling, overnight at 95° C. The pH value of the solution was adjusted to 7 with HCl (1N). Purification via silica gel column (dichloromethane:methanol (1:10)) afforded 35 mg (40%) of 3-(benzo[d][1,3]dioxol-5-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. customto react
  2. customovernight
  3. customat 95° C
  4. customPurification via silica gel column (dichloromethane:methanol (1:10))

Sources & evidence

ORD record
ord-320bf4d8c83d42f4b42d168b923f589e
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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