Ethanol → HCID 90310609, compound

HRID 1524162Notes

Reaction equation

HRID 1524162 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[C:4]([F:11])[C:3]=1[O:12][CH3:13].Br[C:15]1[N:16]=[CH:17][C:18]([NH2:21])=[N:19][CH:20]=1.CCO.C([O-])([O-])=O.[Na+].[Na+]>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.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:15]2[N:16]=[CH:17][C:18]([NH2:21])=[N:19][CH:20]=2)=[C:4]([F:11])[C:3]=1[O:12][CH3:13]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 68810164HCID 68810164, compound

Product 1

HCID 90310609HCID 90310609, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (4-bromo-2-fluoro-3-methoxyphenyl)boronic acid (940 mg, 1.69 mmol) and 5-bromopyrazin-2-amine (1.31 g, 7.56 mmol) was treated with EtOH (12.4 ml), toluene (12.8 ml), and aqueous Na2CO3 (2.0 N, 9.44 ml, 18.9 mmol), and the resulting mixture deoxygenated by sparging with for 10 minutes. Pd(PPh3)4 (218 mg, 0.189 mmol) was then added, and the mixture heated at 80° Celsius for 17 h. The reaction was cooled to rt and then partitioned between saturated aqueous NH4Cl and EtOAc. The organic layer was isolated, dried over MgSO4, and concentrated to dryness. The resultant residue was suspended in DCM and the title compound isolated by filtration (300 mg, 27%), which was used without further purification. Additional product was obtained by concentrating the filtrate to dryness and subjecting the residue to FCC (560 mg, 50%). MS (ESI): mass calcd. for C11HgBrFN3O, 296.99; m/z found, 298.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 8.34 (dd, J=2.6, 1.5, 1H), 8.00 (d, J=1.5, 1H), 7.54-7.49 (m, 2H), 6.78 (s, 2H), 3.90 (d, J=0.6, 3H).

Workup

  1. customthe resulting mixture deoxygenated
  2. customby sparging with for 10 minutes
  3. temperatureThe reaction was cooled to rt
  4. custompartitioned between saturated aqueous NH4Cl and EtOAc
  5. customThe organic layer was isolated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a9a156795661481cb1f56a7884d86e66
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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