Sodium Hydroxide → HCID 59596639, compound

HRID 2264910Notes

Reaction equation

HRID 2264910 reaction equation
C([O:3][C:4]([C:6]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=1[F:32])=[O:5])C.[OH-].[Na+]>>[F:32][C:26]1[CH:27]=[C:28]([I:31])[CH:29]=[CH:30][C:25]=1[NH:24][C:7]1[C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:6]=1[C:4]([OH:5])=[O:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 67211862HCID 67211862, compound

Product 1

HCID 59596639HCID 59596639, compoundYield 89%

Conditions

Temperature
65 °C

Procedure

A mixture of 3-(2-fluoro-4-iodo-phenylamino)-1-(4-methoxy-benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (196 mg, 0.37 mmol), 1M aqueous sodium hydroxide solution (443 μl) and IMS (4 ml) was heated at 65° C. for 2.5 hours. After cooling to ambient temperature the solvent was evaporated, the 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 (5 mL), ethyl acetate (2 mL) and pentane (2 mL) then left to air dry to provide the title compound as a yellow solid (170 mg, 89%). LCMS (method A): RT=7.22 min, M+H+=518.

Workup

  1. temperatureAfter cooling to ambient temperature the solvent
  2. customwas evaporated
  3. dissolutionthe residue was dissolved in water
  4. additionthe pH of the solution was adjusted to 7 by the addition of 1N HCl solution
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water (5 mL), ethyl acetate (2 mL) and pentane (2 mL)
  7. waitthen left to air
  8. customdry

Sources & evidence

ORD record
ord-f4dd3de9b14f4dc6aa0c0fe1dbfdd94b
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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