Sodium Hydroxide → 5-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid

HRID 2076165Notes

Reaction equation

HRID 2076165 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:20]=[N:21][CH:22]=2)[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=1[F:19])=[O:4].[OH-].[Na+]>>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:10]2[N:9]3[CH:20]=[N:21][CH:22]=[C:8]3[CH:7]=[CH:6][C:5]=2[C:3]([OH:4])=[O:2])=[C:13]([F:19])[CH:14]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 591401535-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester

Product 1

HCID 591401635-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acidYield 85.3%

Conditions

Temperature
65 °C

Procedure

To a solution of 5-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester (5.4 g, 15 mmol) in IMS (110 mL) was added aqueous sodium hydroxide (30 mL, 1M, 30 mmol) and the reaction mixture stirred at 65° C. for 1.5 hours. The reaction mixture was concentrated in vacuo to ˜50 mL volume and the resultant solution was acidified to pH ˜2 by addition of aqueous hydrochloric acid (1M) causing a precipitate to form. The precipitate was collected by filtration and dried under vacuum at 35° C. to yield the title compound as a dark tan solid (4.48 g, 85%). LCMS (Method B): RT=2.81 min, M+H+=350/352.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to ˜50 mL volume
  2. additionthe resultant solution was acidified to pH ˜2 by addition of aqueous hydrochloric acid (1M)
  3. customto form
  4. filtrationThe precipitate was collected by filtration
  5. customdried under vacuum at 35° C.

Sources & evidence

ORD record
ord-809c60c4de8a45df8c1d0dfc90fa4ffb
Source dataset
uspto-grants-2011_04
Patent number
US07923456B2

Reaction notes

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