Sodium Carbonate → HCID 10388031, compound

HRID 1744225Notes

Reaction equation

HRID 1744225 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6](Br)[N:7]=1.[O:10]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:26]([O-:29])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[O:10]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([C:11]3[CH:16]=[CH:15][C:14]([O:29][C:26]4[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=4)=[CH:13][CH:12]=3)[N:7]=2)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 6200042-Amino-3,5-dibromopyrazineHCID 27343774-Phenoxyphenylboronic acid

Product 1

HCID 10388031HCID 10388031, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1.00 equivalents (eq.) of 3,5-dibromo-2-aminopyrazine (2) in 3 mL toluene is treated with 10 mole percent tetrakis(triphenylphospine) palladium under nitrogen at room temperature. To this solution is added directly 2.00 eq. of 4-phenoxyphenyl boronic acid at room temperature and then 2 mL Na2CO3 (1.0 M) solution. The reaction vial is capped and the reaction stirred under nitrogen at 90° C. for 10 hours. The toluene layer is separated and removed under reduced pressure, and the resulting oil is purified via flash chromatography to provide (3). MF=C28H21N3O2, MW=431.49 Mass Spec m/z (M++1) 432.14.

Workup

  1. customThe reaction vial is capped
  2. customThe toluene layer is separated
  3. customremoved under reduced pressure
  4. customthe resulting oil is purified via flash chromatography

Sources & evidence

ORD record
ord-61118954107a40439125b39cffde5bae
Source dataset
uspto-grants-2006_03
Patent number
US07015227B2

Reaction notes

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