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

HRID 2175060Notes

Reaction equation

HRID 2175060 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([CH3:37])[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[C:28]2[CH:27]=[C:26](B(O)O)[CH:25]=[CH:24][C:23]1=2.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: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]([CH3:37])([CH3:21])[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[C:28]=4[CH:27]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10353857(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acidHCID 160590464-Boc-1-(6-bromo-2-pyridyl)piperazineHCID 22031701Potassium phosphate, tribasic, monohydrate

Product 1

HCID 672487534-[6-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
80 °C

Procedure

150 mg (0.44 mmol) of 4-(6-bromopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester, 112 mg (0.48 mmol) of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylboronic acid and 202 mg (0.88 mmol) of tripotassium phosphate monohydrate are suspended in 6 ml of ethylene glycol monomethyl ether, degassed a number of times, and 25 mg (0.04 mmol) of bis(triphenylphosphine)-palladium(II) dichloride are added under nitrogen atmosphere. The reaction mixture is stirred at 80° C. for 16 h, cooled to RT, and 20 ml of water are added. This mixture is extracted three times with ethyl acetate, 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. temperaturecooled to RT
  3. extractionThis mixture is extracted three times with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe crude product is purified by means of flash chromatography on silica gel

Sources & evidence

ORD record
ord-5e714a96b7684b788d884a672e756db8
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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