Benzothiazole → methyl 2-(1,3-benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate

HRID 1403417Notes

Reaction equation

HRID 1403417 reaction equation
Cl[C:2]1[C:11]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:17])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=2)[N:3]=1.[S:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[CH:23]1.C([O-])(=O)C.[K+]>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>[S:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[C:2]1[C:11]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:17])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7222BenzothiazoleHCID 517044Potassium AcetateHCID 86670565(S)-methyl 2-chloro-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

Product 1

HCID 70664720methyl 2-(1,3-benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylateYield 20.2%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
170 °C

Procedure

To a solution of methyl 2-chloro-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (300 mg, 0.98 mmol) in 1,3-benzothiazole (266 mg, 1.97 mmol) was added Pd(PPh3)4 (57 mg, 0.05 mmol,) and potassium acetate (193 mg, 1.97 mmol) under an atmosphere of nitrogen. The resulting solution was stirred for 2 h at 170° C. and then quenched by the addition of NH4Cl solution (150 mL), extracted with dichloromethane (3×20 mL) and the organic layers combined and dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography eluting with 1%-5% ethyl acetate in petroleum ether to afford methyl 2-(1,3-benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate as a yellow solid (80 mg, 20%).

Workup

  1. customquenched by the addition of NH4Cl solution (150 mL)
  2. extractionextracted with dichloromethane (3×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography
  7. washeluting with 1%-5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-bb8b2375f12c4b17bc42810a1d32f74c
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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