3-(2-Fluoro-4-iodo-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester → HCID 59596445, compound

HRID 2264900Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=1[F:24])=[O:5])C>[OH-].[Na+]>[F:24][C:18]1[CH:19]=[C:20]([I:23])[CH:21]=[CH:22][C:17]=1[NH:16][C:7]1[C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[N:14]([CH3:15])[C:6]=1[C:4]([OH:5])=[O:3]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 3-(2-fluoro-4-iodo-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (88 mg, 0.20 mmol), 1M aqueous sodium hydroxide solution (220 μl) and IMS (3 ml) was heated at 65° C. for 2 hours. After cooling to ambient temperature the solvent was evaporated, the resultant residue was dissolved in water and the pH of the solution was adjusted to 7 by the addition of 1N HCl solution. The precipitated solid was collected by filtration, washed with water (2 mL) then diethyl ether (2 mL) and left to air dry to provide the title compound as a yellow solid (80 mg, 92%). LCMS (method B): RT=2.11 min, M+H+=412.

Workup

temperatureAfter cooling to ambient temperature the solvent
customwas evaporated
dissolutionthe resultant residue was dissolved in water
additionthe pH of the solution was adjusted to 7 by the addition of 1N HCl solution
filtrationThe precipitated solid was collected by filtration
washwashed with water (2 mL)
waitdiethyl ether (2 mL) and left to air
customdry

Sources & evidence

ORD record: ord-b096c9cd1ece4b55ac3e6d2e05f8b7c8
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855216B2

Reaction notes

Loading…