HCID 10862504, compound → HCID 54597238, compound

HRID 2174663Notes

Reaction equation

HRID 2174663 reaction equation
C([Sn](CCCC)(CCCC)/[C:6](/[F:14])=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)CCC.Br[C:24]1[C:25]([NH2:42])=[N:26][CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])=[CH:32][CH:31]=2)[N:29]=1>C1COCC1.[Pd]>[F:14]/[C:6](/[C:24]1[C:25]([NH2:42])=[N:26][CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH:39]([CH3:40])[CH3:41])(=[O:37])=[O:38])=[CH:32][CH:31]=2)[N:29]=1)=[CH:7]\[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 10862504HCID 10862504, compoundHCID 580843723-Bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

Product 1

HCID 54597238HCID 54597238, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

tributyl-[(E)-1-fluoro-2-phenyl-vinyl]stannane (190 mg, 0.4621 mmol), 3-bromo-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine (164.6 mg, 0.4621 mmol), palladium (9.835 mg, 0.09242 mmol) and cuprous iodide (83.61 mg, 14.85 μL, 0.4390 mmol) were combined in THF (5 mL) and was stirred at 80° C. for 1 hour under microwave conditions. After this time the mixture was filtered over celite, concentrated in vacuo, and the residue was triturated twice in petroleum ether and dried. This material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, and freeze-dried to give the title compound (44 mg, 18.92% Yield). H1 NMR (400.0 MHz, DMSO) H NMR (400.0 MHz, DMSO) δ 1.16-1.19 (d, 6H), 3.45 (m, 1H), 6.88 (d, J=40.7 Hz, 1H), 6.96 (s, 2H), 7.35 (t, J=7.4 Hz, 1H), 7.46 (t, J=7.6 Hz, 2H), 7.73 (d, J=7.5 Hz, 2H), 7.92 (d, J=8.5 Hz, 2H), 8.32 (d, J=8.5 Hz, 2H) and 8.82 (s, 1H) ppm. MS (ES+) 398.0

Workup

  1. filtrationAfter this time the mixture was filtered over celite
  2. concentrationconcentrated in vacuo
  3. customthe residue was triturated twice in petroleum ether
  4. customdried
  5. customThis material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  6. customThe fractions were collected
  7. customfreeze-dried

Sources & evidence

ORD record
ord-5e1726863edd4f96a4a52265747efd6b
Source dataset
uspto-grants-2015_06
Patent number
US09062008B2

Reaction notes

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