Dimethylformamide → HCID 90285208, compound

HRID 1050644Notes

Reaction equation

HRID 1050644 reaction equation
[CH3:1][O-:2].[Na+].Br[C:5]1[CH:18]=[C:17]2[C:19]([CH3:31])([CH3:30])[C:20]3[CH:28]=[C:27](Br)[CH:26]=[C:22]4[C:23]([CH3:25])([CH3:24])[C:13]5[C:14]6[N:15]([C:21]=34)[C:16]2=[C:7]([C:8]([CH3:33])([CH3:32])[C:9]=6[CH:10]=[CH:11][CH:12]=5)[CH:6]=1.CN(C)[CH:36]=[O:37]>[Cu]I>[CH3:1][O:2][C:5]1[CH:18]=[C:17]2[C:19]([CH3:31])([CH3:30])[C:20]3[CH:28]=[C:27]([O:37][CH3:36])[CH:26]=[C:22]4[C:23]([CH3:25])([CH3:24])[C:13]5[C:14]6[N:15]([C:21]=34)[C:16]2=[C:7]([C:8]([CH3:33])([CH3:32])[C:9]=6[CH:10]=[CH:11][CH:12]=5)[CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 90285637HCID 90285637, compound

Product 1

HCID 90285208HCID 90285208, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
100 °C

Procedure

A flame-dried 50 mL Schlenk flask was equipped with sodium methanolate (1.90 g, 35.1 mmol, 6.5 mL; 5.4 M in MeOH), copper(I) iodide (0.77 g, 4.05 mmol) and 2,6-dibromo-4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine (0.21 g, 0.40 mmol), suspended in N,N-dimethylformamide (12.4 mL) and degassed with argon for 30 min. This mixture was stirred under an atmosphere of argon at 100° C. overnight. The reaction was stopped by addition of aqueous NH4Cl solution and the resulting mixture was extracted with CH2Cl2 (3×). The combined organic fractions were dried with MgSO4, filtered and the solvents were evaporated. The crude product was purified by column chromatography (silica, n-hexane/EtOAc 8:1) yielding 2,6-dimethoxy-4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine as a greenish oil (0.12 g, 70%).

Workup

  1. customdegassed with argon for 30 min
  2. additionThe reaction was stopped by addition of aqueous NH4Cl solution
  3. extractionthe resulting mixture was extracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic fractions were dried with MgSO4
  5. filtrationfiltered
  6. customthe solvents were evaporated
  7. customThe crude product was purified by column chromatography (silica, n-hexane/EtOAc 8:1)

Sources & evidence

ORD record
ord-2f7f22d52f1b42e891dc3e58ada206e6
Source dataset
uspto-grants-2016_07
Patent number
US09385326B2

Reaction notes

Loading…