Sodium hydride → HCID 58042370, compound

HRID 2048018Notes

Reaction equation

[H-].[Na+].[CH:3]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[N:7]1)([CH3:5])[CH3:4].[Cl:16][C:17]1[C:18](F)=[CH:19][C:20]([F:30])=[C:21]([CH:29]=1)[C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[O:23]>C1COCC1>[Cl:16][C:17]1[C:18]([O:15][C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[N:6]([CH:3]([CH3:5])[CH3:4])[N:7]=[CH:8]3)=[CH:19][C:20]([F:30])=[C:21]([CH:29]=1)[C:22]([NH:24][S:25]([CH3:28])(=[O:26])=[O:27])=[O:23]

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (60% in mineral oil, 0.012 g, 0.306 mmol) was added to a solution of 1-isopropyl-1H-indazol-5-ol (Preparation 39, 0.045 g, 0.225 mmol) in THF (3.0 mL) while cooling the reaction in an ice bath and stirred for 40 minutes. 5-Chloro-2,4-difluoro-N(methylsulfonyl)benzamide (Preparation 28, 0.076 g, 0.28 mmol) was then added and the reaction was heated at 60° C. for 16 hours. The reaction mixture was concentrated in vacuo and the residue treated with EtOAc (25.0 mL) and washed with water (30.0 mL), followed by brine (30.0 mL). The organic layer was dried over sodium sulfate, filtered, concentrated in vacuo and the residue purified by silica gel chromatography eluting with 2% Methanol in DCM to yield the title compound as a white solid (8.3 mg):

Workup

temperaturewhile cooling
customthe reaction in an ice bath
concentrationThe reaction mixture was concentrated in vacuo
additionthe residue treated with EtOAc (25.0 mL)
washwashed with water (30.0 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customthe residue purified by silica gel chromatography
washeluting with 2% Methanol in DCM

Sources & evidence

ORD record: ord-ee843dd39a8542e5b37a0db4e450cea8
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592629B2

Reaction notes

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