Potassium Carbonate → HCID 90403273, compound

HRID 1049367Notes

Reaction equation

HRID 1049367 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)[CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.[Cl-].[Na+].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>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:27]=[CH:28][C:29]([C:2]3[CH:7]=[C:6]([O:8][C:9]4[C:10]([CH3:18])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=4)[CH:5]=[CH:4][N:3]=3)=[CH:30][CH:31]=2)[CH2:22][CH2:21]1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 179989051-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazineHCID 904036213-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine

Product 1

HCID 90403273HCID 90403273, compoundYield 32.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of Example A4 (0.676 g, 2.55 mmol), 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine (1 g, 3.31 mmol), Pd(PPh3)4 (0.147 g, 0.127 mmol) and K2CO3 (1.055 g, 7.64 mmol) in dioxane (8 mL) and water (2 mL) was sparged with Ar, heated at 90° C. overnight, then cooled to RT. The mixture was treated with brine, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 1-methyl-4-(4-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)phenyl)piperazine (333 mg, 32%). 1H NMR (400 MHz, DMSO-d6): δ 8.55 (d, J=5.6 Hz, 1H), 8.22 (d, J=8.7 Hz, 1H), 7.95 (d, J=8.8 Hz, 2H), 7.81 (d, J=8.7 Hz, 1H), 7.58 (d, J=2.3 Hz, 1H), 6.98 (d, J=8.8 Hz, 2H), 6.94 (dd, J=5.6, 2.3 Hz, 1H), 3.21 (m, 4H), 2.52 (s, 3H), 2.43 (m, 4H), 2.21 (s, 3H); MS (ESI) m/z: 406.2 (M+H+).

Workup

  1. temperaturecooled to RT
  2. extractionextracted with EtOAc (3×)
  3. dry with materialthe combined organics were dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-9bac74f7d5f14aa0934bc9d35d7ffb8e
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

Loading…