1,2-Dichloroethane → HCID 86761631, compound

HRID 2061571Notes

Reaction equation

HRID 2061571 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(O)=O)=[CH:20][CH:19]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:50]([O-])(O)=[O:51].[Na+]>C(Cl)Cl>[Br:17][C:18]1[N:23]=[C:22]([C:50]([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:51])[CH:21]=[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 86761631HCID 86761631, compound

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-1ccebcfc01ba4770b49b239fc98c6798
Source dataset
uspto-grants-2012_10
Patent number
US08283365B2

Reaction notes

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