Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → HCID 67607456, compound

HRID 2175085Notes

Reaction equation

HRID 2175085 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:14]([CH3:19])([CH3:18])[CH2:13][CH2:12][C:11]([CH3:21])([CH3:20])[C:10]=3[CH:9]=2)[N:3]=1.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC.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:22]([O:26][C:27]([N:29]1[CH2:30][CH:31]=[C:32]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[CH:17]=[CH:16][C:15]4[C:14]([CH3:19])([CH3:18])[CH2:13][CH2:12][C:11]([CH3:21])([CH3:20])[C:10]=4[CH:9]=3)[N:3]=2)[CH2:33][CH2:34]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 2

HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 53252486HCID 53252486, compound

Product 1

HCID 67607456HCID 67607456, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

100 mg (0.29 mmol) of 2-bromo-6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridine and 135 mg (0.44 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester are dissolved in 2 ml of 2M sodium carbonate solution and in 2 ml of dimethoxyethane. The reaction mixture is degassed a number of times, 34 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium are added under nitrogen atmosphere, and the mixture is irradiated in the microwave for 30 min, subsequently evaporated, and saturated sodium hydrogencarbonate solution is added. This mixture is 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 silica gel.

Workup

  1. additionare added under nitrogen atmosphere
  2. customthe mixture is irradiated in the microwave for 30 min
  3. customsubsequently evaporated
  4. additionsaturated sodium hydrogencarbonate solution is added
  5. extractionThis mixture is extracted three times with ethyl acetate
  6. dry with materialthe combined organic phases are dried over Na2SO4
  7. customevaporated
  8. customThe crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-21e9a157b01e42119f7cc8c70fff0e7c
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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