1,2-Dichloroethane → HCID 44256467, compound

HRID 388387Notes

Reaction equation

HRID 388387 reaction equation
Cl.[F:2][C:3]([F:16])([F:15])[C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH2:13][NH2:14])=[CH:8][CH:7]=2.[Br:17][C:18]1[N:23]=[CH:22][C:21]([C:24](O)=[O:25])=[CH:20][CH:19]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:17][C:18]1[N:23]=[CH:22][C:21]([C:24]([NH:14][CH2:13][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][C:4]([C:3]([F:2])([F:15])[F:16])=[CH:12]3)=[O:25])=[CH:20][CH:19]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2389326-Bromonicotinic acidHCID 516892Sodium BicarbonateHCID 669093631H-Indole-5-methanamine, 2-(trifluoromethyl)-, hydrochloride (1:1)2×

Product 1

HCID 44256467HCID 44256467, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of {[2-(trifluoromethyl)-1H-indol-5-yl]methyl}amine hydrochloride (Intermediate 5, 1 g, 3.99 mmol), 6-bromo-3-pyridinecarboxylic acid (Matrix Scientific; 0.887 g, 4.39 mmol), EDC (0.841 g, 4.39 mmol), HOBT (0.672 g, 4.39 mmol) and DIPEA (2.8 ml, 16.03 mmol) in DCM (50 ml) was stirred at room temperature for 18 hrs. The mixture was stirred well with saturated aqueous NaHCO3 solution, the organics separated and the aqueous further extracted (EtOAC×3). The combined organics were dried (Phase-Sep cartridge) and evaporated under reduced pressure to a white solid. Trituration with diethyl ether overnight and filtration afforded a crude white solid (1.16 g). A portion (88 mg) was further purified via MDAP to afford the title compound as a white solid (54 mg);

Workup

  1. customthe organics separated
  2. extractionthe aqueous further extracted (EtOAC×3)
  3. customThe combined organics were dried (Phase-Sep cartridge)
  4. customevaporated under reduced pressure to a white solid
  5. filtrationTrituration with diethyl ether overnight and filtration
  6. customafforded a crude white solid (1.16 g)
  7. customA portion (88 mg) was further purified via MDAP

Sources & evidence

ORD record
ord-3f2cbd5c61634f2b9fef7d4993efe2d0
Source dataset
uspto-grants-2013_02
Patent number
US08377941B2

Reaction notes

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