Potassium Carbonate → Methyl 7-(4-((4-chlorophenethyl)carbamoyl) phenoxy)-6-cyano-4-methylchroman-4-carboxylate

HRID 1021362Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1F)[O:9][CH2:8][CH2:7][C:6]2([CH3:18])[C:14]([O:16][CH3:17])=[O:15])#[N:2].C([O-])([O-])=O.[K+].[K+].[Cl:25][C:26]1[CH:43]=[CH:42][C:29]([CH2:30][CH2:31][NH:32][C:33](=[O:41])[C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=2)=[CH:28][CH:27]=1>CN1CCCC1=O>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][CH2:31][NH:32][C:33]([C:34]2[CH:39]=[CH:38][C:37]([O:40][C:12]3[CH:11]=[C:10]4[C:5]([C:6]([CH3:18])([C:14]([O:16][CH3:17])=[O:15])[CH2:7][CH2:8][O:9]4)=[CH:4][C:3]=3[C:1]#[N:2])=[CH:36][CH:35]=2)=[O:41])=[CH:42][CH:43]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Methyl 6-cyano-7-fluoro-4-methylchroman-4-carboxylate (10 mg, 0.040 mmol) was diluted with N-methylpyrrolidone (2 mL) followed by the addition of K2CO3 (28 mg, 0.20 mmol) and N-(4-chlorophenethyl)-4-hydroxybenzamide (11 mg, 0.040 mmol). The reaction was bubbled with argon for 10 minutes and then heated at 110° C. and stirred for 5 hours. The reaction was allowed to cool, loaded directly onto a 25 samplet and eluted on the horizon with 5% ethyl acetate/hexanes to 100% ethyl acetate/hexanes to yield the title compound (12 mg, 59% yield). MS (ESI)=504.9 (M+1).

Workup

customThe reaction was bubbled with argon for 10 minutes
temperatureto cool
washeluted on the horizon with 5% ethyl acetate/hexanes to 100% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-d23f1c78bde64a33837d3f419a3e8591
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716498B2

Reaction notes

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