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Potassium Acetate → tert-butyl 5-(3-(4-(methoxycarbonyl)phenoxy)pyrazin-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate

HRID 555894
Notes
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Reaction equation

HRID 555894 reaction equation
C([O-])(=O)C.[K+].Cl[C:7]1[C:8]([O:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)=[N:9][CH:10]=[CH:11][N:12]=1.CC1(C)C(C)(C)OB([C:32]2[CH2:33][CH2:34][CH2:35][N:36]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:37]=2)O1>CC#N>[CH3:21][O:20][C:18]([C:17]1[CH:22]=[CH:23][C:14]([O:13][C:8]2[C:7]([C:34]3[CH2:33][CH2:32][CH2:37][N:36]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:35]=3)=[N:12][CH:11]=[CH:10][N:9]=2)=[CH:15][CH:16]=1)=[O:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 45031065Methyl 4-(3-chloropyrazin-2-yloxy)benzoateHCID 59327225tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 59351326tert-butyl 5-(3-(4-(methoxycarbonyl)phenoxy)pyrazin-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
80 °C

Procedure

To a mixture of (amphos)2PdCl2 (0.145 g, 0.205 mmol), potassium acetate (1.045 g, 10.65 mmol), methyl 4-(3-chloropyrazin-2-yloxy)benzoate (1.084 g, 4.10 mmol), and tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate (1.900 g, 6.14 mmol) under N2 was added MeCN (7.0 mL) and Ar degassed water (0.70 mL). The reaction mixture was degassed with Ar (10 min) then heated to 80° C. for 20 h. The reaction mixture was diluted with H2O (20 mL) and extracted with Teac (2×10 mL). The combined organic extracts were washed with brine (10 mL), dried (MgSO4), and concentrated. Purification by ISCO (120 g SiO2, 10-100% Teac/hexanes) gave tert-butyl 5-(3-(4-(methoxycarbonyl)phenoxy)pyrazin-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate as a yellow oil.

Workup

  1. customdegassed water (0.70 mL)
  2. customThe reaction mixture was degassed with Ar (10 min)
  3. additionThe reaction mixture was diluted with H2O (20 mL)
  4. extractionextracted with Teac (2×10 mL)
  5. washThe combined organic extracts were washed with brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification by ISCO (120 g SiO2, 10-100% Teac/hexanes)

Sources & evidence

ORD record
ord-aeb6a6566d0340f8ae1d36090ad1a69b
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08053438B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes