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Potassium Carbonate → 3'-(4-Methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid tert-butyl ester

HRID 553478
Notes
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Reaction equation

HRID 553478 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19](Cl)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:27]3[CH:28]=[CH:29][C:24]([CH2:23][O:22][CH3:21])=[CH:25][CH:26]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 37238124-(Methoxymethyl)benzeneboronic acidHCID 11150691Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 673673293'-(4-Methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid tert-butyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve 3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (3.0 g, 10.1 mmol, 1 eq.) in 1,2 dimethoxyethane (6 mL). Add 4-methoxymethyl-benzene boronic acid (2.01 g, 12.12 mmol, 1.2 eq.). Add tetrakis(triphenylphosphine)-palladium (1.17 g, 1.01 mmol, 0.1 eq.) followed by potassium carbonate (3.77 g, 27.3 mmol, 2.7 eq.). Heat the reaction mixture at 100° C. for 17 hr. Partition the reaction mixture between EtOAc and water. Separate layers. Extract the aqueous layer with dichloromethane. Combine organic layers, dry over anhydrous Na2SO4, filter and concentrate. Purify by normal phase chromatography with 10-30% EtOAc/hexane to afford the title preparation (3.7 g, 96% yield). LC MS (ES): m/z=385.3 [M+H].

Workup

  1. customPartition the reaction mixture between EtOAc and water
  2. extractionExtract the aqueous layer with dichloromethane
  3. dry with materialCombine organic layers, dry over anhydrous Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by normal phase chromatography with 10-30% EtOAc/hexane
  7. customto afford the title
  8. custompreparation (3.7 g, 96% yield)

Sources & evidence

ORD record
ord-c9b6dde233204890a5af0041a650976c
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08048884B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes