Dichloromethane → 6-Amino-5-ethylquinoline

HRID 539637Notes

Reaction equation

HRID 539637 reaction equation
C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+].[NH2:10][C:11]1[C:12](Br)=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][CH:15]=[CH:14]2.[CH2:22](B(CC)CC)[CH3:23]>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].O>[NH2:10][C:11]1[C:12]([CH2:22][CH3:23])=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][CH:15]=[CH:14]2

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 7357TriethylboraneHCID 10796Cesium carbonateHCID 127412325-Bromoquinolin-6-amine

Product 1

HCID 582003046-Amino-5-ethylquinolineYield 65.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 183 mg (0.22 mmol) of Pd(dppf)Cl2.CH2Cl2 and 4.38 g (13.44 mmol) of Cs2CO3 in 13 mL of DMF under Argon atmosphere was added a solution of 500 mg (2.24 mmol) of 6-amino-5-bromoquinoline (commercially available from ACES Pharma Product List). Triethylborane in hexanes (2.91 mL of 1.0 M solution) was added, and the reaction was heated to 50° C. for 22 hours, then poured into 50 mL of water, and extracted with diethyl ether. The combined ether layers were washed with saturated aqueous NaHCO3 solution and brine, dried over MgSO4, filtered, and concentrated under reduced pressure to an oil. The oil was purified via silica gel chromatography, eluting with 0 to 50% EtOAc/hexanes to give 386 mg (65.8%) of 6-amino-5-ethylquinoline as e a colorless oil. MS (ESI): m/z 173.2 (M+H)+.

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined ether layers were washed with saturated aqueous NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to an oil
  6. customThe oil was purified via silica gel chromatography
  7. washeluting with 0 to 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-47f904543135449992e89f2d99d37cab
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

Loading…