Triethylamine → 5-Bromo-N-(2,3-difluorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

HRID 269498Notes

Reaction equation

HRID 269498 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([OH:13])=O)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[F:20][C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[NH2:28].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[F:20][C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[NH:28][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[NH:8][CH:9]=1)=[O:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 782782,3-DifluoroanilineHCID 260764485-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Product 1

HCID 598322925-Bromo-N-(2,3-difluorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (950 mg, 3.94 mmol) in DCM (20 mL) and DMF (0.1 mL) was added oxalyl chloride (600 mg, 4.72 mmol) slowly. The mixture was stirred at RT for 1 h. To this suspension was then added a solution of 2,3-difluorophenyl amine (610 mg, 4.72 mmol) and triethylamine (800 mg, 7.91 mmol) in DCM (5 mL). The reaction was kept at RT for another 2 h. The solvent was then evaporated, the residue was washed water, and dried for direct use. MS (ES+): m/e=352 (M+H); LC: 3.5 min.

Workup

  1. waitThe reaction was kept at RT for another 2 h
  2. customThe solvent was then evaporated
  3. washthe residue was washed water
  4. customdried for direct use
  5. custom3.5 min.

Sources & evidence

ORD record
ord-a34ab36d89354c898b20b6b293574ef4
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

Loading…