Potassium Carbonate → HCID 86700054, compound

HRID 1428103Notes

Reaction equation

HRID 1428103 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[Br:32][C:33]1[C:34]([NH2:40])=[N:35][CH:36]=[C:37](I)[CH:38]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.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>[Br:32][C:33]1[C:34]([NH2:40])=[N:35][CH:36]=[C:37]([C:15]2[CH:14]=[CH:13][C:4]([O:5][CH2:6][CH2:7][N:8]3[CH2:9][CH2:10][CH2:11][CH2:12]3)=[C:3]([O:2][CH3:1])[CH:16]=2)[CH:38]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 176094413-Bromo-5-iodopyridin-2-amineHCID 68934529HCID 68934529, compound

Product 1

HCID 86700054HCID 86700054, compoundYield 61.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1-{2-[2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl}pyrrolidine (5.81 g), tetrakis(triphenylphosphine)palladium (0.97 g) and potassium carbonate (6.94 g) were added to a solution of 3-bromo-5-iodopyridin-2-amine (5.00 g) in dioxane (40 ml) and water (4 ml) at room temperature. The reaction mixture was stirred at 80° C. overnight. The reaction mixture was returned to room temperature and a saturated aqueous sodium bicarbonate solution was added, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=50:1->20:1->10:1 (v/v)] to give 4.03 g of the title compound as an oily substance.

Workup

  1. customwas returned to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [chloroform:methanol=50:1->20:1->10:1 (v/v)]

Sources & evidence

ORD record
ord-3f538baf6e22472cb49e0cb81c7e88bc
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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