Dichloromethane → HCID 58154518, compound

HRID 2359431Notes

Reaction equation

HRID 2359431 reaction equation
Cl[C:2]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]2[C:4](=[C:5]([C:16]([NH:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[O:17])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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]>[C:25]1([C:2]2[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]3[C:4](=[C:5]([C:16]([NH:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)=[O:17])[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 58154773HCID 58154773, compound

Product 1

HCID 58154518HCID 58154518, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 2-chloro-N-(pyridin-3-yl)-3-(trifluoromethyl)quinoline-8-carboxamide (136 mg, 0.39 mmol), phenylboronic acid (62 mg, 0.51 mmol), Pd(dppf)Cl2.CH2Cl2 (39 mg, 0.048 mmol), K2CO3 (167 mg, 1.2 mmol) in dioxane/H2O (4:1, 3 ml) was heated (85° C.×2 hours) under a blanket of Nitrogen. The reaction mixture was evaporated, and the residue was triturated with ethyl acetate. The mixture was filtered, concentrated and the residue was purified by prep. HPLC to give 2-phenyl-N-(pyridin-3-yl)-3-(trifluoromethyl)quinoline-8-carboxamide as a white powder (62 mg, 41% yield). MS (ESI) calcd for C22H14F3N3O (m/z): 393.11. found: 394 [M+1].

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was triturated with ethyl acetate
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. customthe residue was purified by prep

Sources & evidence

ORD record
ord-c5ba08b3a4b346569d962038f2c6c055
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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