Potassium Carbonate → HCID 86720790, compound

HRID 1776078Notes

Reaction equation

HRID 1776078 reaction equation
[C:1]1([N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:23][C:24]1[CH:29]=[N:28][C:27](Br)=[CH:26][N:25]=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:23][C:24]1[N:25]=[CH:26][C:27]([C:11]2[CH:12]=[CH:13][C:8]([N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:9][CH:10]=2)=[N:28][CH:29]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 114704212,5-dibromopyrazineHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 86720790HCID 86720790, compoundYield 68.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
85 °C

Procedure

A mixture of (4-(diphenylamino)phenyl)boronic acid (3.26 g, 11.3 mmol), 2,5-dibromopyrazine (5.82 g, 22.6 mmol), Pd(PPh3)4 (0.635 g, 0.55 mmol), K2CO3 (3.45 g, 25 mmol) in dioxane/water (100 mL/16 mL) was degassed and heated at about 85° C. for about 20 hours. The resulting mixture was poured into ethyl acetate (250 mL), washed with brine, dried over Na2SO4, loaded on silica gel and purified by flash column using eluents of hexanes to hexanes/dichloromethane 4:1. After removal of solvent, a yellow solid (Compound 19) was obtained (3.1 g, in 68.2% yield).

Workup

  1. customwas degassed
  2. additionThe resulting mixture was poured into ethyl acetate (250 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified by flash column
  6. customAfter removal of solvent

Sources & evidence

ORD record
ord-12d566bb4fd149e58fea850ddaab8101
Source dataset
uspto-grants-2016_02
Patent number
US09263681B2

Reaction notes

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