Dimethylformamide → HCID 178421630, compound

HRID 1911081Notes

Reaction equation

HRID 1911081 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[C:26]2[C:14](=[C:15]([CH3:28])[C:16]3[NH:17][C:18]4[CH:19]=[CH:20][C:21]([OH:27])=[CH:22][C:23]=4[C:24]=3[CH:25]=2)[CH:13]=[CH:12][N:11]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:9][C:10]1[C:26]2[C:14](=[C:15]([CH3:28])[C:16]3[NH:17][C:18]4[CH:19]=[CH:20][C:21]([O:27][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[CH:22][C:23]=4[C:24]=3[CH:25]=2)[CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178421629HCID 178421629, compound2×

Product 1

HCID 178421630HCID 178421630, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of benzyl bromide (230 μl, 1.9 mMol) in acetone (6 ml) is added at room temperature, over 15 minutes, to a mixture containing 1-chloro-9-hydroxy-5-methyl-6H-pyrido[4,3-b]carbazole (Compound 10) (490 mg, 1.73 mMol), acetone (7 ml), DMF (2 ml) and K2CO3 (400 mg). The assembly is left stirring for 24 h, then the solvents are subsequently evaporated under vacuum. Water is then added (30 ml). The assembly is again left stirring for 24 h. The solid form is recovered by filtration, washed with water, then dried at room temperature for 18 h. An inter-mediate, 1-chloro-9-benzyloxy-5-methyl-6H-pyrido[4,3-b]carbazole (330 mg, 51% yield) is obtained, after chromatography through a silica column using dichloromethane/ethyl acetate (from 99%/1% to 95%/5%) as eluent. The product obtained is identical to that obtained according to the method described in J. Chem. Soc. Perkin Trans. 1, 1979, 1706. The mixture of 1-chloro-9-benzyloxy-5-methyl-6H-pyrido[4,3-b]carbazole obtained above (320 mg, 0.86 mMol), DMF (7 ml) and sodium methoxide (30% solution in methanol, 10 ml) is heated under reflux for 20 h. The reaction mixture is poured into 60 ml of water, then left stirring for 2 h. The solid formed, recovered by filtration, is washed with water then dried. 280 mg (88% yield) of the expected compound 9-benzyloxy-1-methoxy-5-methyl-6H-pyrido[4,3-b]carbazole (Compound 7) are then obtained, after chromatography through a silica column using dichloromethane/ethyl acetate (from 99.5%/0.5% to 99%/1%) as eluent. The proton NMR spectrum of Compound 7 is the following:

Workup

  1. waitThe assembly is left
  2. customthe solvents are subsequently evaporated under vacuum
  3. additionWater is then added (30 ml)
  4. waitThe assembly is again left
  5. stirringstirring for 24 h
  6. filtrationThe solid form is recovered by filtration
  7. washwashed with water
  8. customdried at room temperature for 18 h

Sources & evidence

ORD record
ord-7aaa9dff390748d7aea5093ac351da1b
Source dataset
uspto-grants-2013_12
Patent number
US08604048B2

Reaction notes

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