Dichloromethane → HCID 90314275, compound

HRID 1524156Notes

Reaction equation

HRID 1524156 reaction equation
Br[C:2]1[C:3]([S:8]([CH:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)(=[O:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[F:23][C:24]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[CH:26][C:25]=1[C:39]1[N:40]=[CH:41][C:42]([NH2:45])=[N:43][CH:44]=1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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]>[NH2:45][C:42]1[N:43]=[CH:44][C:39]([C:25]2[CH:26]=[CH:27][C:28]([C:2]3[C:3]([S:8]([CH:11]4[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]4)(=[O:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=3)=[CH:29][C:24]=2[F:23])=[N:40][CH:41]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amineHCID 90314726HCID 90314726, compound

Product 1

HCID 90314275HCID 90314275, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl 3-(3-bromopyridin-2-ylsulfonyl)pyrrolidine-1-carboxylate (205 mg, 60% purity, 0.320 mmol), 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazin-2-amine (100 mg, 0.320 mmol), Pd(dppf)Cl2.CH2Cl2 (23 mg, 0.030 mmol), and Na2CO3 (101 mg, 0.950 mmol) in DMF (6 mL) was stirred at 100° C. for 16 h under N2 before cooling to rt and concentrating it to dryness. The resultant residue was subjected to FCC followed by HPLC purification to give the title compound (150 mg, 99%). MS (ESI): mass calcd. For C24H26FN5O4S 499.17; m/z found, 521.9 [M+Na]+.

Workup

  1. concentrationconcentrating it to dryness
  2. customfollowed by HPLC purification

Sources & evidence

ORD record
ord-be1dae149ccf44b6bd50d418b820b1d4
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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