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

HRID 2243310Notes

Reaction equation

HRID 2243310 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[CH:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)=O.C(N(C(C)C)CC)(C)C.[B-].[Na+].P([O-])(O)(O)=O.[K+].[N:43]1[C:51]2[CH:50]=[CH:49][N:48]=[CH:47][C:46]=2[NH:45][C:44]=1[C:52]1[C:64]2[C:63]3[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=3)[CH:57]([NH2:65])[C:56]=2[CH:55]=[CH:54][CH:53]=1>C(O)C>[N:43]1[C:51]2[CH:50]=[CH:49][N:48]=[CH:47][C:46]=2[NH:45][C:44]=1[C:52]1[C:64]2[C:63]3[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=3)[CH:57]([NH:65][CH2:15][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][CH:21]=[CH:20]4)[C:56]=2[CH:55]=[CH:54][CH:53]=1

Participants

8

Reactant 6

HCID 81531DiisopropylethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 516951Monobasic potassium phosphateHCID 589040Indole-5-carboxaldehydeHCID 22959485VertellusHCID 56594091HCID 56594091, compound

Product 1

HCID 59208187n-[4-(3h-Imidazo[4,5-c]pyridin-2-yl)-9h-fluoren-9(r,s)-yl]-(1h-indol-5-yl-methyl)-amineYield 32.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 5-ml three-necked flask, dissolve 74 mg of 4-(3H-imidazo[4,5-c]pyridin-2-yl)-fluorene-9(R,S)-amine, isolated as the dihydrochloride, in 0.5 ml of ethanol, add 45 mg of 5-formyl-indole and 70 μL of diisopropylethylamine and stir for 2 hours 30 minutes at room temperature. Then add 28 mg of sodium hydroborate and stir for 18 hours at room temperature. Pour the reaction mixture into 5 ml of a saturated aqueous solution of potassium dihydrogen phosphate, then extract 3 times with 10 ml of dichloromethane. After purification on silica gel, eluting with mixtures of dichloromethane and methanol (98-2, then 96-4 by volume), we obtain 34 mg of N-[4-(3H-imidazo[4,5-c]pyridin-2-yl)-9H-fluoren-9(R,S)-yl]-(1H-indol-5-yl-methyl)-amine, in the form of a white solid with the following characteristics:

Workup

  1. stirringstir for 18 hours at room temperature
  2. extractionextract 3 times with 10 ml of dichloromethane
  3. customAfter purification on silica gel
  4. washeluting with mixtures of dichloromethane and methanol (98-2

Sources & evidence

ORD record
ord-130bad20c8d849d98e60d83a6d369c4e
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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