2,6-Dibromopyridine → HCID 53252486, compound

HRID 2175084Notes

Reaction equation

HRID 2175084 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:26]=[CH:25][C:24]3[C:23]([CH3:28])([CH3:27])[CH2:22][CH2:21][C:20]([CH3:30])([CH3:29])[C:19]=3[CH:18]=2)O1>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>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:26]2[CH:17]=[CH:18][C:19]3[C:20]([CH3:30])([CH3:29])[CH2:21][CH2:22][C:23]([CH3:28])([CH3:27])[C:24]=3[CH:25]=2)[N:3]=1

Participants

6

Reactant 2

HCID 122742,6-DibromopyridineHCID 112439294,4,5,5-Tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane

Product 1

HCID 53252486HCID 53252486, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

200 mg (0.84 mmol) of 2,6-dibromopyridine and 265 mg (0.84 mmol) of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane are dissolved in 6 ml of 2M sodium carbonate solution and in 2.5 ml of dimethoxyethane. The reaction mixture is degassed a number of times, and 49 mg (0.04 mmol) of tetrakis(triphenylphosphine)palladium are added under nitrogen atmosphere, the mixture is stirred at 80° C. for 16 h and subsequently irradiated in the microwave for 30 min. The reaction mixture is evaporated, and saturated sodium hydrogencarbonate solution is added. This mixture is extracted three times with ethyl acetate and three times with dichloromethane, the combined organic phases are dried over Na2SO4 and evaporated. The crude product is reacted further without further purification.

Workup

  1. additionare added under nitrogen atmosphere
  2. customsubsequently irradiated in the microwave for 30 min
  3. customThe reaction mixture is evaporated
  4. additionsaturated sodium hydrogencarbonate solution is added
  5. extractionThis mixture is extracted three times with ethyl acetate and three times with dichloromethane
  6. dry with materialthe combined organic phases are dried over Na2SO4
  7. customevaporated
  8. customThe crude product is reacted further without further purification

Sources & evidence

ORD record
ord-ca9bde2f379d4fa2b1b68ee66bf54ab7
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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