Acetonitrile → 6-chloro-5-[4-(propan-2-yl)phenyl]-1H-indole-3-carboxylic acid

HRID 338538Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=1.C(#N)C.[Mn]([O-])(=O)(=O)=[O:26].[K+].S(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:26])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 30 °C

Procedure

A vial was charged with 6-chloro-5-[4-(propan-2-yl)phenyl]-1H-indole-3-carbaldehyde, 1 mL acetonitrile, and 500 uL of a 1.0M solution of potassium permanganate in water. The vial was sealed and heated to 30° C. for 16 hrs. Sodium bisulfite (72 mg, 1.0 mmol) was then added and the reaction heated to 30° C. for 1 hr. The reaction was then filtered, and the solvent removed in vacuo. The residue was then purified by reverse phase prep HPLC to give the title compound. MS (AP−) 312 (M−H)−. RT=2.378 Column Xbridge C18 2.1×50 mm 5 μm, Temperature 50° C. Mobile Phase A=0.05% NH4OH in water. Mobile Phase B=100% acetonitrile. Gradient: Initial 5% B Time 0.00 mins, 5% B Time 0.50 mins, 5% B Time 3.40 mins, 100% B Time 4.20 mins, 100% B Time 4.21 mins, 5% B Time 4.70 mins, 5% B Flow rate, 0.8 mL/min Injection volume 2 μL. Agilent 1200 HPLC/1956 MSD/SEDEX 75 ELSD Ionization Mode API-ES Polarity Negative.

Workup

customThe vial was sealed
temperaturethe reaction heated to 30° C. for 1 hr
filtrationThe reaction was then filtered
customthe solvent removed in vacuo
customThe residue was then purified by reverse phase prep HPLC

Sources & evidence

ORD record: ord-84524175db124186a44546087b514a0c
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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