Potassium Phosphate, Tribasic → (R)-methyl 3-(sec-butylamino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylate

HRID 1403454Notes

Reaction equation

HRID 1403454 reaction equation
[C@H:1]([NH:5][C:6]1[C:7](OS(C(F)(F)F)(=O)=O)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=2)([CH2:3][CH3:4])[CH3:2].[F:28][C:29]1[CH:30]=[CH:31][C:32]2[O:36][C:35](B(O)O)=[CH:34][C:33]=2[CH:40]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C@H:1]([NH:5][C:6]1[C:7]([C:35]2[O:36][C:32]3[CH:31]=[CH:30][C:29]([F:28])=[CH:40][C:33]=3[CH:34]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=2)([CH2:3][CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 22260896(5-Fluoro-1-benzofuran-2-yl)boronic acidHCID 86670569(R)-methyl 3-(sec-butylamino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

Product 1

HCID 70664795(R)-methyl 3-(sec-butylamino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (R)-methyl 3-(sec-butylamino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (400 mg, crude) in dioxane (5 mL) was added 5-fluorobenzofuran-2-ylboronic acid (441 mg, 2.45 mmol), K3PO4 (620 mg, 2.94 mmol), and Pd(PPh3)4 (57 mg, 0.05 mmol). The resulting solution was stirred for 1 h at 90° C. and then quenched by the addition of dichloromethane (200 mL) and washed with water (3×50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (5% ethyl acetate in petroleum ether) to afford (R)-methyl 3-(sec-butylamino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylate as a yellow solid (100 mg, 24% 2 steps).

Workup

  1. customquenched by the addition of dichloromethane (200 mL)
  2. washwashed with water (3×50 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography (5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-2f7b1bdb3faf43938309070138377252
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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