Potassium Carbonate → HCID 90403273, compound

HRID 2279011Notes

Reaction equation

HRID 2279011 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.[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

7

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 3

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

Conditions

Temperature
90 °C

Procedure

A mixture of Example A6 (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), K2CO3 (1.055 g, 7.64 mmol) and Pd(PPh3)4 (0.147 g, 0.127 mmol) in dioxane (8 mL) was sparged with Ar and heated at 90° C. overnight. The mixture was cooled to RT, treated with brine, extracted with EtOAc (4×) 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, 1 H), 8.22 (d, J=8.7 Hz, 1 H), 7.95 (d, J=8.8 Hz, 2 H), 7.81 (d, J=8.7 Hz, 1 H), 7.58 (d, J=2.3 Hz, 1 H), 6.98 (d, J=8.8 Hz, 2 H), 6.94 (dd, J=5.6, 2.3 Hz, 1 H), 3.24-3.18 (m, 4 H), 2.52 (s, 3 H), 2.45-2.41 (m, 4 H), 2.21 (s, 3H); MS (ESI) m/z: 406.2 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with EtOAc (4×)
  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-5883d732a0794d0587d88b4bf6c1d1e0
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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