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Water → 4-[6-(5,5-Dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2175061
Notes
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Reaction equation

HRID 2175061 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](Br)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]1([CH3:41])[CH2:31][CH2:30][CH2:29][C:28]2[CH:27]=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=[CH:24][C:23]1=2.O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:26]3[CH:25]=[CH:24][C:23]4[C:22]([CH3:41])([CH3:21])[CH2:31][CH2:30][CH2:29][C:28]=4[CH:27]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 160590464-Boc-1-(6-bromo-2-pyridyl)piperazineHCID 18407952Tripotassium phosphate trihydrateHCID 532501122-(5,5-Dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 672484724-[6-(5,5-Dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 80192-MethoxyethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

500 mg (1.46 mmol) of 4-(6-bromopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester, 460 mg (1.61 mmol) of 2-(5,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 620 mg (2.92 mmol) of tripotassium phosphate trihydrate are suspended in 10 ml of ethylene glycol monomethyl ether, degassed a number of times, and 82 mg (0.04 mmol) of bis(triphenylphosphine)palladium(II) dichloride are added under nitrogen atmosphere. The reaction mixture is treated in an ultrasound bath for 10 min, subsequently irradiated in the microwave at 100° C. for 90 min, 50 ml of water and 50 ml of ethyl acetate are added, and the mixture is filtered. The residue is discarded. The organic phase of the filtrate is separated off, and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by means of flash chromatography on silica gel.

Workup

  1. additionare added under nitrogen atmosphere
  2. additionThe reaction mixture is treated in an ultrasound bath for 10 min
  3. customsubsequently irradiated in the microwave at 100° C. for 90 min
  4. filtrationthe mixture is filtered
  5. customThe organic phase of the filtrate is separated off
  6. extractionthe aqueous phase is extracted three times with ethyl acetate
  7. dry with materialThe combined organic phases are dried over Na2SO4
  8. customevaporated
  9. customThe crude product is purified by means of flash chromatography on silica gel

Sources & evidence

ORD record
ord-5f504cbfd54b4893bcc02a95d4601278
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09062015B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes