Sodium Carbonate → HCID 86616962, compound

HRID 1929841Notes

Reaction equation

HRID 1929841 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:8][C:6]1[N:7]=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=2)[C:3]([NH2:9])=[N:4][CH:5]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 6200042-Amino-3,5-dibromopyrazine

Product 1

HCID 86616962HCID 86616962, compoundYield 84.3%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2.5 g of 3,5-dibromo-pyrazin-2-ylamine in 60 ml 1,2-dimethoxy-ethane is added 1.19 g tetrakis(triphenylphosphine) palladium at room temperature and stirred for ½ hour. To the resulting orange solution is added a solution of 2.65 g sodium carbonate in 30.0 mL water and 1.56 g of p-chlorophenylboronic acid and the mixture is stirred for 18 hours at 100° C. The starting material is completely consumed as evidenced by tlc. The reaction mixture was partitioned between water and ethyl acetate; the phases are separated and the organic phase is dried over sodium sulfate evaporated and purified by chromatography on silica gel with heptane:ethyl acetate=1:1. to yield 2.37 g of the title compound as light yellow crystals, MS (ISP) 284.0, 286.0 (M+H)+.

Workup

  1. stirringthe mixture is stirred for 18 hours at 100° C
  2. customThe starting material is completely consumed
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customthe phases are separated
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. customevaporated
  7. custompurified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-60303edd861349228b776085b8e5ea44
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

Loading…