Potassium Carbonate → HCID 67248263, compound

HRID 2175068Notes

Reaction equation

HRID 2175068 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16](Cl)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:29]2[CH:38]=[CH:37][C:36]3[C:35]([CH3:40])([CH3:39])[CH2:34][CH2:33][C:32]([CH3:42])([CH3:41])[C:31]=3[CH:30]=2)O1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.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>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([C:38]3[CH:29]=[CH:30][C:31]4[C:32]([CH3:42])([CH3:41])[CH2:33][CH2:34][C:35]([CH3:40])([CH3:39])[C:36]=4[CH:37]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 112439294,4,5,5-Tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolaneHCID 59252248Tert-butyl 4-(2-chloropyridin-4-YL)piperazine-1-carboxylate

Product 1

HCID 67248263HCID 67248263, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

202 mg (0.68 mmol) of 4-(2-chloropyridin-4-yl)piperazine-1-carboxylic acid tert-butyl ester, 256 mg (0.81 mmol) of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane and 187 mg (1.36 mmol) of potassium carbonate are dissolved in 6 ml of acetonitrile and 650 μl of water. The reaction mixture is degassed a number of times, 78 mg (0.07 mmol) of tetrakis(triphenylphosphine)palladium are added under nitrogen atmosphere, the mixture is irradiated in the microwave at 120° C. for 90 min, subsequently diluted with water and extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by column chromatography on RP silica gel.

Workup

  1. additionare added under nitrogen atmosphere
  2. customthe mixture is irradiated in the microwave at 120° C. for 90 min
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. customThe crude product is purified by column chromatography on RP silica gel

Sources & evidence

ORD record
ord-8e47ce99693d4228b077bbdf298fc515
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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