Triethylamine → HCID 71061270, compound

HRID 875477Notes

Reaction equation

HRID 875477 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[NH:18]1[C:26]2[C:21](=[CH:22][N:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([N:18]1[C:26]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[CH:20]=[CH:19]1)=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 92205-AzaindoleHCID 65578Oxalyl chlorideHCID 679472-Chloro-6-fluorobenzoic acid

Product 1

HCID 71061270HCID 71061270, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-chloro-6-fluorobenzoic acid (2.5 g, 14.32 mmol) in dichloromethane (20 mL), oxalyl chloride (3.029 ml, 28.64 mmol) was added at 0° C. After stirring at the same temperature for 15 min, dimethylfromamide (2-3 drops) was added, and the reaction was allowed to stir at room temperature for 1.5 hours. The reaction mixture was cooled and concentrated on rotary evaporator. The residue was taken up in dichloromethane (20 mL) and treated with 5-azaindole (1.72 g, 14.51 mmol) and triethylamine (6.1 mL, 43.52 mmol). The resulting reaction mixture was allowed to stir at room temperature for 20 hours. The reaction mixture was concentrated under vacuum, diluted with water (50 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was removed under rotary evaporator. The product was isolated by silica gel column chromatography using ethyl acetate (25%) in hexanes as eluent to yield (2-chloro-6-fluorophenyl)(1H-pyrrolo[3,2-c]pyridin-1-yl)methanone (1.56 g, 39.5%).

Workup

  1. additiondimethylfromamide (2-3 drops) was added
  2. stirringto stir at room temperature for 1.5 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated on rotary evaporator
  5. customThe resulting reaction mixture
  6. stirringto stir at room temperature for 20 hours
  7. concentrationThe reaction mixture was concentrated under vacuum
  8. additiondiluted with water (50 mL)
  9. extractionextracted with ethyl acetate (2×100 mL)
  10. washThe combined organic layer was washed with saturated aqueous solution of sodium bicarbonate
  11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customthe solvent was removed under rotary evaporator
  14. customThe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-e044ac21e33b424582b1fde88d8e21a0
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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