Ethyl Bromide → methyl 4-(3-amino-6-(1-ethyl-1H-pyrazol-4-yl)pyrazin-2-yl)-2-fluorobenzoate

HRID 596098Notes

Reaction equation

HRID 596098 reaction equation
[NH2:1][C:2]1[C:3]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([F:23])[CH:14]=2)=[N:4][C:5]([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)=[CH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH3:32]>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([F:23])[CH:14]=2)=[N:4][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:31][CH3:32])[CH:12]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 118045485methyl 4-(3-amino-6-(1H-pyrazol-4-yl) pyrazin-2-yl)-2-fluorobenzoate

Product 1

HCID 118045915methyl 4-(3-amino-6-(1-ethyl-1H-pyrazol-4-yl)pyrazin-2-yl)-2-fluorobenzoateYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To methyl 4-(3-amino-6-(1H-pyrazol-4-yl) pyrazin-2-yl)-2-fluorobenzoate (45 mg, 0.115 mmol) in DMF (2 mL) was added potassium carbonate (47.6 mg, 0.345 mmol), followed by bromoethane (0.017 mL, 0.230 mmol). The reaction mixture was stirred at room temperature for 48 h. The reaction mixtures was partitioned between ethylacetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered, evaporated and purified by flash chromatography eluting with 0-60% of EtOAc (contains 10% of MeOH)/heptane to yield the desired product (25 mg, 64%, 80% purity). LCMS (m/z): 342.0 (MH+), 0.73 min.

Workup

  1. customThe reaction mixtures
  2. customwas partitioned between ethylacetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by flash chromatography
  9. washeluting with 0-60% of EtOAc (contains 10% of MeOH)/heptane

Sources & evidence

ORD record
ord-18eef34053d94b1e9a4a2f2bb2e3e98e
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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