Water → HCID 86682947, compound

HRID 1497085Notes

Reaction equation

HRID 1497085 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:20])[CH:8]=2)[N:3]=1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C.O>CN(C=O)C>[Cl:20][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[C:11]([C:12]#[N:13])=[C:10]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31268PyrrolidineHCID 86682946HCID 86682946, compound

Product 1

HCID 86682947HCID 86682947, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

2,6-Dichloro-4-phenyl-quinoline-3-carbonitrile (30 mg, 100 μmol, Eq: 1.00), pyrrolidine (14.3 mg, 16.6 μl, 201 μmol, Eq: 2) and triethylamine (30.4 mg, 41.9 μl, 301 μmol, Eq: 3) were dissolved in DMF (0.5 ml) and the reaction mixture was heated to 120° C. for 20 min in a microwave. Then water was added and the mixture was extracted with ethyl acetate (3×). The combined organic layers were dried with Na2SO4 and evaporated to dryness. The remaining residue was purified by column chromatography (silica gel, DCM/heptane 1:1) to afford the title compound as yellow solid (28 mg). MS (ESI): 334.2 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. customevaporated to dryness
  4. customThe remaining residue was purified by column chromatography (silica gel, DCM/heptane 1:1)

Sources & evidence

ORD record
ord-cad2b64391d345c19663a2a13fc5dfc3
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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