Dichloromethane → HCID 90315324, compound

HRID 1524056Notes

Reaction equation

HRID 1524056 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.[CH3:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O)(=[O:18])=[O:17].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]>[CH3:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[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)(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27735392-(Methylsulfonyl)phenylboronic AcidHCID 20567052HCID 20567052, compound

Product 1

HCID 90315324HCID 90315324, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
70 °C

Procedure

5-(4-Bromophenyl)pyrazin-2-amine (51 mg, 0.20 mmol), (2-(methylsulfonyl)phenyl) boronic acid (61 mg, 0.31 mmol), K2CO3 (85 mg, 0.61 mmol) and Pd(dppf)Cl2.CH2Cl2 (15 mg, 0.020 mmol) were weighed into a sealable vial containing a stir-bar. The vial was sealed and evacuated before backfilling with argon and adding deoxygenated DMSO (0.8 mL). The vial was heated at 70° Celsius for 3 hours by which point the starting material had been consumed. The vial was cooler to rt, diluted with MeOH (1 mL), filtered with a syringe filter, and the filtrate subjected to HPLC purification to provide the title compound. MS (ESI): mass calcd. for C17H15N3O2S, 325.39; m/z found, 326.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.32 (dd, J=8.1, 1.4, 2H), 8.26 (dd, J=8.0, 1.4, 1H), 8.00-7.90 (m, 2H), 7.74-7.64 (m, 1H), 7.64-7.56 (m, 3H), 7.41 (dd, J=7.5, 1.4, 1H), 2.70 (s, 3H).

Workup

  1. additioncontaining a stir-bar
  2. customThe vial was sealed
  3. customevacuated
  4. additionadding
  5. customdeoxygenated DMSO (0.8 mL)
  6. customhad been consumed
  7. customwas cooler to rt
  8. additiondiluted with MeOH (1 mL)
  9. filtrationfiltered with a syringe
  10. filtrationfilter
  11. customthe filtrate subjected to HPLC purification

Sources & evidence

ORD record
ord-fca7fb3e2a854d2980720540a27f5a2b
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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