Dichloromethane → HCID 90312970, compound

HRID 1524050Notes

Reaction equation

HRID 1524050 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)=[CH:4][CH:3]=1.[C:15]([NH:19][S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O)(=[O:22])=[O:21])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:14][C:11]1[N:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:24]3[C:23]([S:20]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:21])=[O:22])=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:3][CH:4]=2)=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-HCID 20567052HCID 20567052, compound

Product 1

HCID 90312970HCID 90312970, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
70 °C

Procedure

To a 5 mL sealable vial equipped with a stir bar were added 5-(4-bromophenyl)pyrazin-2-amine (40 mg, 0.16 mmol), (2-(N-(tert-butyl)sulfamoyl)phenyl)-boronic acid (62 mg, 0.24 mmol), K2CO3 (66 mg, 0.48 mmol) and Pd(dppf)Cl2.CH2Cl2 (12 mg, 0.016 mmol). The vial was then sealed, evacuated, backfilled with argon and charged with argon sparged DMSO (0.64 mL). The vial was heated at 70° Celsius for 15 hours. The reaction mixture was cooled to rt diluted with ethyl acetate (2 mL) and water (2 mL), the layers separated and the aqueous layer further extracted with ethyl acetate (3×10 mL). The combined organic extracts were then dried with Na2SO4 and concentrated to dryness. The crude product was purified by HPLC to give the title compound. MS (ESI): mass calcd. for C20H22N4O2S, 382.15; m/z found, 383.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.48-8.39 (d, J=1.5, 1H), 8.23-8.18 (dd, J=8.0, 1.4, 1H), 8.18-8.15 (d, J=1.4, 1H), 7.99-7.95 (d, J=8.4, 1H), 7.65-7.61 (m, 2H), 7.61-7.55 (m, 1H), 7.55-7.46 (m, 1H), 7.38-7.31 (dd, J=7.5, 1.4, 1H), 3.70 (s, 1H), 1.25 (s, 1H), 1.03 (s, 9H).

Workup

  1. customTo a 5 mL sealable vial equipped with a stir bar
  2. customThe vial was then sealed
  3. customevacuated
  4. additioncharged with argon
  5. customsparged DMSO (0.64 mL)
  6. temperatureThe reaction mixture was cooled to rt
  7. additiondiluted with ethyl acetate (2 mL) and water (2 mL)
  8. customthe layers separated
  9. extractionthe aqueous layer further extracted with ethyl acetate (3×10 mL)
  10. dry with materialThe combined organic extracts were then dried with Na2SO4
  11. concentrationconcentrated to dryness
  12. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-34bb2cfd27174f78a4384b75cb20b08b
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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