Potassium Carbonate → tert-butyl ((1S,2S)-2-((5-(trifluoromethyl)-3-vinylpyrazin-2-yl)amino)cyclopentyl)carbamate

HRID 1750542Notes

Reaction equation

HRID 1750542 reaction equation
Br[C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.[CH:26](B1OC(C)(C)C(C)(C)O1)=[CH2:27].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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>[CH:26]([C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1)=[CH2:27]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 118308064tert-butyl ((1S,2S)-2-((3-bromo-5-(trifluoromethyl)pyrazin-2-yl)amino)cyclopentyl)carbamate

Product 1

HCID 118308332tert-butyl ((1S,2S)-2-((5-(trifluoromethyl)-3-vinylpyrazin-2-yl)amino)cyclopentyl)carbamate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of tert-butyl N-[(1S,2S)-2-{[3-bromo-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate (650 mg, 1.53 mmol), 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS number 75927-49-0; 942 mg, 6.11 mmol), tetrakis(triphenylphosphine)palladium (177 mg, 0.15 mmol) and potassium carbonate (845 mg, 6.11 mmol) in 1,4-dioxane (5 ml) and water (0.8 ml) was subjected to microwave irradiation at 120° C. for 1 hour. The reaction was partitioned between ethyl acetate (10 ml) and water (10 ml). The aqueous layer was further extracted with ethyl acetate (3×20 ml). The combined organics were washed with brine (20 ml), filtered through a hydrophobic frit and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-50% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customirradiation at 120° C. for 1 hour
  2. customThe reaction was partitioned between ethyl acetate (10 ml) and water (10 ml)
  3. extractionThe aqueous layer was further extracted with ethyl acetate (3×20 ml)
  4. washThe combined organics were washed with brine (20 ml)
  5. filtrationfiltered through a hydrophobic frit
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (silica, 0-50% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-df15de982a6147cbb98da4c3563e5513
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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