Potassium Carbonate → HCID 86720788, compound

HRID 1776077Notes

Reaction equation

HRID 1776077 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:18]1[CH:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][CH:19]=1)[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[CH3:17].Br[C:34]1[CH:39]=[N:38][C:37]([Br:40])=[CH:36][N:35]=1.C([O-])([O-])=O.[K+].[K+]>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:40][C:37]1[N:38]=[CH:39][C:34]([C:21]2[CH:20]=[CH:19][C:18]([N:9]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=3[CH3:17])[C:3]3[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])=[CH:23][CH:22]=2)=[N:35][CH:36]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 114704212,5-dibromopyrazineHCID 86720789HCID 86720789, compound2×

Product 1

HCID 86720788HCID 86720788, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-(2,4-dimethylphenyl)-2,4-dimethyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline (Compound 17) (6.0 g, 14 mmol), 2,5-dibromopyrazine (7.74 g, 30 mmol), Pd(PPh3)4 (0.5 g, 0.43 mmol), K2CO3 (4.14 g, 30 mmol) in dioxane/water (80 mL/17 mL) was degassed and heated at about 80° C. overnight. The resulting mixture was poured into ethyl acetate (200 mL), washed with brine, dried over Na2SO4, then loaded on silica gel and purified by flash column using eluents of hexanes to hexanes/dichloromethane 9:1 to 6:1 to 7:3. The desired yellow fraction was collected, and a yellow solid (Compound 18) was obtained after removal of solvents (3.83 g, 60% yield).

Workup

  1. customwas degassed
  2. additionThe resulting mixture was poured into ethyl acetate (200 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified by flash column
  6. customThe desired yellow fraction was collected

Sources & evidence

ORD record
ord-fe0dc1412411431cab580533be6df289
Source dataset
uspto-grants-2016_02
Patent number
US09263681B2

Reaction notes

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