Sodium Carbonate → HCID 21865556, compound

HRID 857306Notes

Reaction equation

HRID 857306 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:33])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:17]=[C:18]([C:26]([S:29]([CH3:32])(=[O:31])=[O:30])([CH3:28])[CH3:27])[CH:19]=[C:20]4[C:25]=3[N:24]=[CH:23][CH:22]=[CH:21]4)[CH:11]=2)=[CH:4][CH:3]=1.[CH3:34][S:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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]>[CH3:32][S:29]([C:26]([C:18]1[CH:19]=[C:20]2[C:25](=[C:16]([C:12]3[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=3)[C:9]([NH:8][C:5]3[CH:6]=[N:7][C:2]([C:39]4[CH:40]=[CH:41][C:36]([S:35][CH3:34])=[CH:37][CH:38]=4)=[CH:3][CH:4]=3)=[O:33])[CH:17]=1)[N:24]=[CH:23][CH:22]=[CH:21]2)([CH3:28])[CH3:27])(=[O:31])=[O:30]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 21865605HCID 21865605, compound

Product 1

HCID 21865556HCID 21865556, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(6-Chloro-pyridin-3-yl)-3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-benzamide, 4-methylsulfanyl-phenyl boronic acid (2 eq), PdCl2(dppf)2 (0.05 eq) and aqueous Na2CO3 (4 eq) in DME (0.04M from benzamide) was stirred at 100° C. for 12 h. The resulting mixture was poured in water and extracted with EtOAc (2×). The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated. Flash chromatography (EtOAc) afforded the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7540f267a67647d187b76fafb7718204
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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