Dichloromethane → N-(2-(3-fluorophenyl)quinolin-8-yl)thiazole-4-carboxamide

HRID 2359395Notes

Reaction equation

HRID 2359395 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][C:13]([C:15]3[N:16]=[CH:17][S:18][CH:19]=3)=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C(Cl)Cl>COCCOC.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]>[F:20][C:21]1[CH:26]=[C:25]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([NH:12][C:13]([C:15]4[N:16]=[CH:17][S:18][CH:19]=4)=[O:14])[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 27339863-Fluorophenylboronic acidHCID 58154776HCID 58154776, compound

Product 1

HCID 58154579N-(2-(3-fluorophenyl)quinolin-8-yl)thiazole-4-carboxamideYield 24.6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

A solution of N-(2-chloroquinolin-8-yl)thiazole-4-carboxamide (29 mg, 0.100 mmol), 3-fluorophenylboronic acid (28 mg, 2 eq.), CsCO3 (65 mg, 2 eq.), Pd(dppf)Cl2.DCM (4 mg, 0.05 eq.) in DME (2 mL) was microwave heated (140° C.×15 min.). The reaction was filtered and concentrated. The residue was diluted with ethyl acetate, washed with saturated aqueous NaHCO3, dried (Na2SO4) and concentrated. The product was purified by column chromatography (0 to 100% EtOAc in Pentane) to obtain 8.6 mg of N-(2-(3-fluorophenyl)quinolin-8-yl)thiazole-4-carboxamide. MS (ESI) calcd for C19H13FN3OS (m/z): 350.08. found: 350.1 [M+1].

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe product was purified by column chromatography (0 to 100% EtOAc in Pentane)

Sources & evidence

ORD record
ord-b5c8fe3f17674216b68bd51e0425a86e
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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