Potassium Carbonate → Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-6-cyano-2,2-dimethylchroman-4-carboxylate

HRID 1047997Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1F)[O:9][C:8]([CH3:15])([CH3:14])[CH2:7][CH:6]2[C:16]([O:18][CH3:19])=[O:17])#[N:2].C([O-])([O-])=O.[K+].[K+].[Cl:26][C:27]1[CH:44]=[CH:43][C:30]([CH2:31][CH2:32][NH:33][C:34](=[O:42])[C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)=[CH:29][CH:28]=1>CN1CCCC1=O>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:31][CH2:32][NH:33][C:34]([C:35]2[CH:40]=[CH:39][C:38]([O:41][C:12]3[CH:11]=[C:10]4[C:5]([CH:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:7][C:8]([CH3:15])([CH3:14])[O:9]4)=[CH:4][C:3]=3[C:1]#[N:2])=[CH:37][CH:36]=2)=[O:42])=[CH:43][CH:44]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Methyl 6-cyano-7-fluoro-2,2-dimethylchroman-4-carboxylate (19 mg, 0.072 mmol) was diluted with N-methylpyrrolidone (2 mL) followed by the addition of K2CO3 (25 mg, 0.18 mmol) and N-(4-chlorophenethyl)-4-hydroxybenzamide (20 mg, 0.072 mmol). The reaction was bubbled with argon for 10 minutes and then heated at 110° C. for 6 hours. After cooling, the reaction mixture was loaded directly onto a Biotage 25 column and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield the title compound (2.0 mg, 5.3% yield).

Workup

customThe reaction was bubbled with argon for 10 minutes
temperatureAfter cooling
washeluted with 5% ethyl acetate/hexanes to 100% ethyl acetate

Sources & evidence

ORD record: ord-eb18c3cadb7245b2adcc6d293a370a1a
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569522B2

Reaction notes

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