2-Chloroquinoline → HCID 117732316, compound

HRID 1772752Notes

Reaction equation

HRID 1772752 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]2[C:10]([CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]4)=[N:21][CH:22]=3)[N:6]2[CH:36]=1.[H-].[Na+].Cl[C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[N:41]=1>CN(C=O)C>[N:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:48]=[CH:49][C:40]=1[O:1][CH2:2][C:3]1[N:4]=[C:5]2[C:10]([CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:27][CH2:28]4)=[N:21][CH:22]=3)[N:6]2[CH:36]=1

Participants

5

Reactant 3

HCID 119282-ChloroquinolineHCID 24758Sodium hydrideHCID 117733765HCID 117733765, compound

Product 1

HCID 117732316HCID 117732316, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Into a 10 mL round-bottom flask was placed a solution of compound 90j (150 mg, 0.300 mmol) in DMF (2 mL), followed by the addition of sodium hydride (30.0 mg, 1.25 mmol) at 0° C. The mixture was stirred for 15 min at 0° C., and 2-chloroquinoline (74.2 mg, 0.460 mmol) was added. The reaction mixture was stirred overnight at 70° C. Upon cooling, the reaction was quenched with water. The resulting mixture was extracted with DCM (3×10 mL). The combined organic layers were concentrated under reduced pressure. The resultant residue was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:3 v/v)) to obtain compound 91a as a light yellow solid (130 mg, 69% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C35H39N7O4: 622.3 (M+H). found: 622.2.

Workup

  1. customInto a 10 mL round-bottom flask was placed
  2. stirringThe reaction mixture was stirred overnight at 70° C
  3. temperatureUpon cooling
  4. customthe reaction was quenched with water
  5. extractionThe resulting mixture was extracted with DCM (3×10 mL)
  6. concentrationThe combined organic layers were concentrated under reduced pressure
  7. customThe resultant residue was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:3 v/v))

Sources & evidence

ORD record
ord-72def7d325c749d583ce4e33dc1353b5
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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