Aluminum(III) Chloride → HCID 67468758, compound

HRID 1777725Notes

Reaction equation

HRID 1777725 reaction equation
C([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:26]=[C:25]4[C:20]([CH:21]=[CH:22][CH:23]=[N:24]4)=[C:19]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[N:18]=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1(OC)C=CC=CC=1>[NH:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:26]=[C:25]4[C:20]([CH:21]=[CH:22][CH:23]=[N:24]4)=[C:19]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[N:18]=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 67464620HCID 67464620, compound2×

Product 1

HCID 67468758HCID 67468758, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent2×

Conditions

Temperature
110 °C

Procedure

To a solution of 7-(1-benzyl-1H-indol-4-yl)-5-morpholin-4-yl-1,6-naphthyridine, 4 (64 mg, 0.13 mmol, 1 eq) in dry anisole (1.5 mL) was added a suspension of AlCl3 in dry anisole (1.5 mL). The mixture was then heated at 110° C. for 0.5 h. Once cooled down, it was partitioned with H2O (15 mL) and extracted with EtOAc (3×20 mL) and CH2Cl2 (20 mL). The combined organic extracts were then dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with CH2Cl2/MeOH (1:0-49:1) to yield the product, G, as a pale yellow solid (7.8 mg, 15%).

Workup

  1. temperatureOnce cooled down
  2. customit was partitioned with H2O (15 mL)
  3. extractionextracted with EtOAc (3×20 mL) and CH2Cl2 (20 mL)
  4. dry with materialThe combined organic extracts were then dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was further purified by silica gel column chromatography with CH2Cl2/MeOH (1:0-49:1)
  7. customto yield the product, G

Sources & evidence

ORD record
ord-d1328b780fcf49baaf5298890aecb74f
Source dataset
uspto-grants-2016_02
Patent number
US09266879B2

Reaction notes

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