Potassium Carbonate → N-(4'-(5-Aminopyrazin-2-yl)-3'-fluoro-[1,1'-biphenyl]-2-yl)propane-2-sulfonamide

HRID 1523779Notes

Reaction equation

HRID 1523779 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[C:4]([F:15])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:22][CH:23]([S:25]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)(=[O:27])=[O:26])[CH3:24]>CS(C)=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>[NH2:14][C:11]1[N:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[NH:28][S:25]([CH:23]([CH3:24])[CH3:22])(=[O:27])=[O:26])=[CH:3][C:4]=2[F:15])=[N:9][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amineHCID 90313758(2-(1-Methylethylsulfonamido)phenyl)boronic acid

Product 1

HCID 77844067N-(4'-(5-Aminopyrazin-2-yl)-3'-fluoro-[1,1'-biphenyl]-2-yl)propane-2-sulfonamideYield 9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine (309 mg, 1.15 mmol) in DMSO (5 mL) was added K2CO3 (317 mg, 2.3 mmol). The mixture was sparged with N2 several times. Pd(PPh3)4 (66 mg, 0.058 mmol) and (2-(1-methylethylsulfonamido)-phenyl)boronic acid (280 mg, 1.15 mmol) were added and the resultant mixture sparged with N2. The mixture was heated at 80° Celsius for 14 hours before cooling to rt and diluting with water (70 mL). The precipitate was collected, rinsed with water, air dried, and then purified by HPLC to give the title compound (40 mg, 9%). MS (ESI): mass calcd. for C19H19FN4O2S, 386.12; m/z found, 387.1 [M+H]+. 1H NMR (300 MHz, CD3OD) δ 8.72 (s, 1H), 8.25 (d, J=1.2, 1H), 8.16 (m, 1H), 7.50 (d, J=7.8, 1H), 7.47-7.34 (m, 5H), 3.15-3.03 (m, 1H), 1.23 (d, J=6.8, 6H).

Workup

  1. customThe mixture was sparged with N2 several times
  2. customthe resultant mixture sparged with N2
  3. temperaturebefore cooling to rt
  4. additiondiluting with water (70 mL)
  5. customThe precipitate was collected
  6. washrinsed with water, air
  7. customdried
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-e95cf2de420546ec84a4cac947fc5ef5
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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