Sodium Carbonate → HCID 86616962, compound

HRID 1159237Notes

Reaction equation

HRID 1159237 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-d3fb10ece999415492d024e4686e7403
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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