HCID 15594672, compound → HCID 90313278, compound

HRID 1524167Notes

Reaction equation

HRID 1524167 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[N:12][CH:11]=[CH:10][N:9]=1.[F:14][C:15]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=[CH:17][C:16]=1[C:30]1[N:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=1>CC(C1C=C(C(C)C)C(C2C=CC=C(P(C3CCCCC3)C3CCCCC3)C=2)=C(C(C)C)C=1)C.C1C=[C-]C(C2C(N)=CC=CC=2)=CC=1.Cl[Pd+]>[F:14][C:15]1[CH:20]=[C:19]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[CH:13]=[N:12][CH:11]=[CH:10][N:9]=2)[CH:18]=[CH:17][C:16]=1[C:30]1[N:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=1

Participants

4

Reactant 2

HCID 15594672HCID 15594672, compoundHCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine

Product 1

HCID 90313278HCID 90313278, compound

Reagents, catalysts & solvents 1

HCID 72376365[2-(2-Aminophenyl)phenyl]-chloro-palladium dicyclohexyl-[3-(2,4,6-triisopropylphenyl)phenyl]phosphaneCatalyst

Conditions

Temperature
45 °C

Procedure

2-(2-Chlorophenyl)pyrazine (58 mg, 0.31 mmol), 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazin-2-amine (88 mg, 0.28 mmol) and chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (4.4 mg, 0.0060 mmol) were placed into a sealable 5 mL vial equipped with a stir-bar. The vial was sealed, evacuated and backfilled with argon three times. To this vial was added separately deoxygenated THF (0.56 mL) and K3PO4 (1.1 mL, 0.5 M). The vial was then heated at 45° Celsius for 1 hour before cooling to rt diluting with brine (5 mL), and extracting with EtOAc (1×5 mL, 3×10 mL). The combined organic extracts were then dried with sodium sulfate, filtered, and concentrated to dryness. The crude product was purified via FCC to provide the title compound. MS (ESI): mass calcd. for C20H14FN5, 343.12; m/z found, 344.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.65-8.59 (dd, J=2.6, 1.6, 1H), 8.47-8.42 (d, J=2.6, 1H), 8.33-8.31 (dd, J=2.2, 1.4, 1H), 8.31-8.29 (d, J=1.5, 1H), 8.04-8.02 (d, J=1.5, 1H), 7.79-7.73 (m, 1H), 7.72-7.69 (m, 1H), 7.64-7.53 (m, 3H), 7.11-6.87 (m, 2H).

Workup

  1. customvial equipped with a stir-bar
  2. customThe vial was sealed
  3. customevacuated
  4. additionTo this vial was added separately deoxygenated THF (0.56 mL) and K3PO4 (1.1 mL, 0.5 M)
  5. temperaturebefore cooling to rt
  6. additiondiluting with brine (5 mL)
  7. extractionextracting with EtOAc (1×5 mL, 3×10 mL)
  8. dry with materialThe combined organic extracts were then dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customThe crude product was purified via FCC

Sources & evidence

ORD record
ord-ef1978952a184d5280bf835300bf0f29
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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