Pyridine → HCID 59804515, compound

HRID 2423228Notes

Reaction equation

HRID 2423228 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)([CH3:3])[CH3:2].N1C=CC=CC=1.ClC(Cl)(O[C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[NH2:44][C:45]1[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=1>ClCCl>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:29]([NH:44][C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=2)=[O:35])=[CH:11]1)([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 1049PyridineHCID 7813p-ToluidineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 67240517HCID 67240517, compound

Product 1

HCID 59804515HCID 59804515, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cooled solution of 1-(2-isopropylphenyl)-1H-indole (117 mg, 0.50 mmol) and pyridine (42.5 μL, 0.0524 mmol) in dichloromethane (anhydrous) (3.0 mL) under a nitrogen atmosphere is added triphosgene (146 mg, 0.50 mmol) and the reaction allowed to stir with warming to ambient temperature for overnight. An aliquot of the reaction solution (600 μL, 0.1 mmol) is removed and added to a solution of triethylamine (28 μL, 0.1 mmol), N,N-dimethylaminopyridine (2.4 mg, 0.2 mmol), and p-toluidine (12 mg, 0.11 mmol) in dichloromethane (anhydrous) (1.0 mL) and stirred at ambient temperature for 14 hours). The reaction mixture was concentrated and the residue purified by RP HPLC to give Example 51. LC/MS (ESI+) 369.5 (M+H)+.

Workup

  1. stirringstirred at ambient temperature for 14 hours)
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue purified by RP HPLC
  4. customto give Example 51

Sources & evidence

ORD record
ord-171cee83aa174f54bf2fdb6157b479be
Source dataset
uspto-grants-2011_06
Patent number
US07960569B2

Reaction notes

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