Diisopropylethylamine → n-[4-(3h-Imidazo[4,5-c]pyridin-2-yl)-9h-fluoren-9(r,s)-yl]-(1h-indol-6-ylmethyl)-amine

HRID 2243311Notes

Reaction equation

HRID 2243311 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[N:15]1[C:23]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[NH:17][C:16]=1[C:24]1[C:36]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]([NH2:37])[C:28]=2[CH:27]=[CH:26][CH:25]=1.[CH:38]([C:40]1[CH:48]=[C:47]2[C:43]([CH:44]=[CH:45][NH:46]2)=[CH:42][CH:41]=1)=O.C(N(C(C)C)CC)(C)C.[B-].[Na+]>C(O)C>[N:15]1[C:23]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[NH:17][C:16]=1[C:24]1[C:36]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]([NH:37][CH2:38][C:40]3[CH:48]=[C:47]4[C:43]([CH:44]=[CH:45][NH:46]4)=[CH:42][CH:41]=3)[C:28]=2[CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 27734351H-Indole-6-carboxaldehydeHCID 22959485VertellusHCID 56594091HCID 56594091, compound

Product 1

HCID 59208179n-[4-(3h-Imidazo[4,5-c]pyridin-2-yl)-9h-fluoren-9(r,s)-yl]-(1h-indol-6-ylmethyl)-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Carry out the procedure as in Example 18, starting from 94 mg of dihydrochloride of 4-(3H-imidazo[4,5-c]pyridin-2-yl)-fluorene-9(R,S)-amine, 55 mg of 6-formyl-indole and 90 μL of diisopropylethylamine in 0.7 ml of ethanol for 2 hours at room temperature, then add 28 mg of sodium hydroborate and stir for 1 hour at room temperature. After purification on silica gel, eluting with mixtures of dichloromethane and methanol (95-5 by volume), we obtain 58 mg of N-[4-(3H-imidazo[4,5-c]pyridin-2-yl)-9H-fluoren-9(R,S)-yl]-(1H-indol-6-ylmethyl)-amine, in the form of a pale pink solid with the following characteristics:

Workup

  1. customAfter purification on silica gel
  2. washeluting with mixtures of dichloromethane and methanol (95-5 by volume), we

Sources & evidence

ORD record
ord-3771c7a750444ab491e67c5c5d863396
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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