Dimethylformamide → HCID 71767782, compound

HRID 1771448Notes

Reaction equation

HRID 1771448 reaction equation
[H-].[Na+].[CH:3]1([C:16](OC)=O)[C:12]2[C:7]3[C:8](=[CH:13][CH:14]=[CH:15][C:6]=3[CH2:5][O:4]1)[CH:9]=[CH:10][CH:11]=2.C[N:21]([CH:23]=O)[CH3:22].IC.CCOC(C)=O.C(Cl)Cl.[CH2:36]([N:38](CC)CC)C>C1COCC1.C1(C)C=CC=CC=1>[CH3:16][C:3]1([C:22]2[NH:38][CH2:36][CH2:23][N:21]=2)[C:12]2[C:7]3[C:8](=[CH:13][CH:14]=[CH:15][C:6]=3[CH2:5][O:4]1)[CH:9]=[CH:10][CH:11]=2

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22169412HCID 22169412, compoundHCID 117925871HCID 117925871, compound

Product 1

HCID 71767782HCID 71767782, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of NaH (0.18 g), methyl 1,3-dihydrobenzo[de]isochromene-1-carboxylate (0.5 g) and DMF (2 ml), toluene (2 ml) and THF (6 ml) was stirred in ice-bath temperature. Iodomethane (0.7 ml) was added and the mixture was stirred at ambient temperature for 3 hrs. The intermediate methyl 1-methyl-1,3-dihydrobenzo[de]isochromene-1-carboxylate (0.3 g) was purified with separation method A and E (EtOAc/heptanes), and the title compound was synthesized using the procedure of synthesis method A step 3 and separation method E (EtOAc/DCM/triethyl amine 10/20/1). (Yield 0.1 g).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 3 hrs
  2. customThe intermediate methyl 1-methyl-1,3-dihydrobenzo[de]isochromene-1-carboxylate (0.3 g) was purified with separation method A and E (EtOAc/heptanes)

Sources & evidence

ORD record
ord-20387b5ff457405095a7eb1d32186bb2
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

Loading…