Sodium Hydroxide → 1-Benzyl-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid

HRID 623737Notes

Reaction equation

[CH2:1]([N:8]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:9]1[C:24]([O:26]CC)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.O>[CH2:1]([N:8]1[C:12]([C:13]([F:14])([F:15])[F:16])=[CH:11][C:10]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[C:9]1[C:24]([OH:26])=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 1-benzyl-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate (2.59 g, 6.35 mmol) in dry THF (15 mL) was added a solution of NaOH (3.9 g, 98 mmol) in H2O (15 mL). The reaction mixture was stirred overnight at 80° C. An additional portion of NaOH (4.25 g, 106 mmol) was added and the reaction mixture was stirred at 100° C. during 7 h. The organic solvent was evaporated and the residue was acidified with aqueous 5 M HCl (55 mL). The product was extracted with EtOAc (3×20 mL). The combined organic layer was washed with brine (3×20 mL) and dried (Na2SO4). The remaining oil was triturated with heptane (20 mL). The off-white solids were filtered off to give 1.29 g (51%) ACI-06.

Workup

stirringthe reaction mixture was stirred at 100° C. during 7 h
customThe organic solvent was evaporated
extractionThe product was extracted with EtOAc (3×20 mL)
washThe combined organic layer was washed with brine (3×20 mL)
dry with materialdried (Na2SO4)
customThe remaining oil was triturated with heptane (20 mL)
filtrationThe off-white solids were filtered off
customto give 1.29 g (51%) ACI-06

Sources & evidence

ORD record: ord-59e1ed40479844d89bc7654de8e543a8
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302988B2

Reaction notes

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