Tetrahydrofuran → 2-[(E)-2-(3-Dimethylamino-phenyl)-vinyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

HRID 2235408Notes

Reaction equation

HRID 2235408 reaction equation
N[C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[NH:29][C:13]3=[CH:14][C:15]4[C:16]([CH3:28])([CH3:27])[C:17](=[O:26])[N:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:19]=4[CH:20]=[C:12]3[N:11]=2)[CH:5]=[CH:6][CH:7]=1.[C:30]([BH3-])#[N:31].[CH2:33]1COCC1>C(O)(=O)C>[CH3:33][N:31]([CH3:30])[C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[NH:29][C:13]3=[CH:14][C:15]4[C:16]([CH3:28])([CH3:27])[C:17](=[O:26])[N:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:19]=4[CH:20]=[C:12]3[N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 498716Cyano-borohydride2×HCID 674266922-[(E)-2-(3-amino-phenyl)-vinyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

Product 1

HCID 593009282-[(E)-2-(3-Dimethylamino-phenyl)-vinyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution 2-[(E)-2-(3-amino-phenyl)-vinyl]-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (170 mg) in dry THF (2.5 ml) and acetic acid (0.3 ml) is added p-formaldehyde (41.5 mg; 1,31 mmol) and resin-bound cyanoborohydride (MP-cyanoborohydride; Argonaut) (1.23 g; 2.50 mmol). The mixture is gently stirred under an inert atmosphere (Ar) at RT for 48 h. After completion of the reaction the mixture is filtered and concentrated in vacuo. The desired compound (43.0 mg) is obtained by preparative RP-HPLC.

Workup

  1. customAfter completion of the reaction the mixture
  2. filtrationis filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b1f02effd40433d99aedb11b24b83e9
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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