Potassium Carbonate → tert-butyl 1-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylate

HRID 1810100Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:17]([C:19]1[CH:20]=[C:21]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:22]=[CH:23][C:24]=1F)#[N:18].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[C:17]([C:19]1[CH:20]=[C:21]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:22]=[CH:23][C:24]=1[N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)#[N:18]

Participants

Conditions

Temperature: 95 °C

Procedure

tert-Butyl 1H-indole-5carboxylate (0.800 g, 3.68 mmol), methyl 2-(3-cyano-4-fluorophenyl)acetate (0.593 g, 3.07 mmol), and potassium carbonate (0.509 g, 3.68 mmol) were combined in 15 mL of DMSO and the reaction mixture was stirred at 95° C. for 24 hours. Reaction was diluted with ethyl acetate washed twice with water, dried over magnesium sulfate and concentrated. Silica gel chromatography eluting with a gradient of 5% ethyl acetate/hexanes to 60% ethyl acetate/hexanes gave tert-butyl 1-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylate (0.380 g, 0.973 mmol, 32%). MS (APCI)=390.9 (M+1).

Workup

customReaction
washwashed twice with water
dry with materialdried over magnesium sulfate
concentrationconcentrated
washSilica gel chromatography eluting with a gradient of 5% ethyl acetate/hexanes to 60% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-5ade1c33e1ed4c20974eb92ca6d5572f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362056B2

Reaction notes

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