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

HRID 1047987Notes

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][CH:6]2[C:14]([O:16][CH3:17])=[O:15])#[N:2].C([O-])([O-])=O.[K+].[K+].[Cl:24][C:25]1[CH:42]=[CH:41][C:28]([CH2:29][CH2:30][NH:31][C:32](=[O:40])[C:33]2[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=2)=[CH:27][CH:26]=1>CN1CCCC1=O>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][CH2:30][NH:31][C:32]([C:33]2[CH:38]=[CH:37][C:36]([O:39][C:12]3[CH:11]=[C:10]4[C:5]([CH:6]([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:35][CH:34]=2)=[O:40])=[CH:41][CH:42]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Methyl 6-cyano-7-fluorochroman-4-carboxylate (50 mg, 0.21 mmol) was diluted with 1-methyl-2-pyrrolidinone (2 mL) followed by the addition of K2CO3 (147 mg, 1.1 mmol) and N-(4-chlorophenethyl)-4-hydroxybenzamide (59 mg, 0.21 mmol). The reaction was bubbled with argon for 10 minutes and then heated to 110° C. and stirred for 6 hours. After the reaction was allowed to cool, it was loaded directly onto a Biotage 25 column and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (50 mg, 48% yield). MS (ESI)=490.9 (M+1).

Workup

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

Sources & evidence

ORD record: ord-d762d2f26d5a49d3bc878854622be6c4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569522B2

Reaction notes

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