tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate → 5,6-Dihydro-N,N-dimethyl-4H-pyrrolo(3,2,1ij)quinolin-5-amine

HRID 327478Notes

Reaction equation

HRID 327478 reaction equation
Br[CH2:2][C:3]1[C:11]2[N:10]=[CH:9]N(C(OC(C)(C)C)=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:19]([N:22]([CH:26]([C:32](OCC)=O)[C:27](OCC)=O)[CH2:23]CC)CC>C1COCC1.CCOCC>[CH3:19][N:22]([CH3:23])[CH:26]1[CH2:32][C:7]2[C:11]3=[C:3]([CH:2]=[CH:9][N:10]3[CH2:27]1)[CH:4]=[CH:5][CH:6]=2

Participants

4

Reactant 2

HCID 15744964tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylateHCID 15744966Diethyl (dipropylamino)propanedioate

Product 1

HCID 114697185,6-Dihydro-N,N-dimethyl-4H-pyrrolo(3,2,1ij)quinolin-5-amine

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

This compound was prepared by following the procedure of Example 18, but substituting methyl 7-(bromomethyl)-1H-indole-1-carboxylate for t-butyl 4-(bromomethyl)-1H-benzimidazole-1-carboxylate and diethyl (dimethylamino)malonte for diethyl (dipropylamino)malonate. The bulk of the product was converted to the maleate salt, mp 114°-115° C. from THF/ether.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-556cf091629349e592814e7e8c44d29f
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

Loading…