Nitrogen → HCID 67286052, compound

HRID 1909012Notes

Reaction equation

HRID 1909012 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:25][CH3:26])[CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13](B2OC(C)(C)C(C)(C)O2)[C:14]=1[CH3:15])([CH3:4])([CH3:3])[CH3:2].[CH3:28][O:29][C:30](=[O:38])[C:31]1[CH:36]=[CH:35][N:34]=[C:33](Br)[CH:32]=1.N#N>O1CCOCC1.O.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>[CH3:28][O:29][C:30]([C:31]1[CH:36]=[CH:35][N:34]=[C:33]([C:13]2[CH:12]=[N:11][CH:10]=[C:9]([CH2:8][N:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:27])[CH2:25][CH3:26])[C:14]=2[CH3:15])[CH:32]=1)=[O:38]

Participants

7

Reactant 3

HCID 947NitrogenHCID 38477682-Bromo-isonicotinic acid methyl esterHCID 67287026HCID 67287026, compound

Product 1

HCID 67286052HCID 67286052, compoundYield 69.2%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl-[4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-ylmethyl]-carbamic acid tert-butyl ester (1.5 g, 5.1 mmol) and 2-bromo-isonicotinic acid methyl ester (1.3 g, 6.1 mmol) were suspended in 1,4-dioxane (25 mL). To the mixture was added K3PO4.3H2O (0.90 g, 4.52 mmol, 1 M in water). The reaction was degassed with N2 and PdCl2(PPh3)2 (72 mg, 0.1 mmol) was added. The reaction was heated to 60° C. for 3 hours. The mixture was then diluted with water and neutralised to pH 7. The mixture was concentrated in vacuo, to remove organic solvent, and then partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (×3). The combined organic layers were washed with water, brine, dried (MgSO4) and then evaporated to dryness. Purification by SiO2 chromatography gave the title compound (1.36 g). m/z 386 (M+H)+

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated in vacuo
  3. customto remove organic solvent
  4. custompartitioned between water and EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc (×3)
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness
  9. customPurification by SiO2 chromatography

Sources & evidence

ORD record
ord-780d9dbc787644c1ba06b0139636043b
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

Loading…