Cesium carbonate → HCID 46928113, compound

HRID 1626384Notes

Reaction equation

[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]([C:19]([O:21][CH3:22])=[O:20])[CH2:14][CH2:15][O:16]3)=[CH:11][C:10]=2[C:23]#[N:24])=[CH:6][CH:5]=1)(=[O:3])[NH2:2].Cl[C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][N:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C[C@@H](P(C(C)(C)C)C(C)(C)C)[C]1[C](P(C2CCCCC2)C2CCCCC2)[CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1.[Fe].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:35][C:34]([F:37])([F:36])[C:31]1[CH:32]=[CH:33][C:28]([NH:2][C:1]([C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]3[CH:18]=[C:17]4[C:12]([CH:13]([C:19]([O:21][CH3:22])=[O:20])[CH2:14][CH2:15][O:16]4)=[CH:11][C:10]=3[C:23]#[N:24])=[CH:25][CH:26]=2)=[O:3])=[N:29][CH:30]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Methyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate (58 mg, 0.17 mmol), 2-chloro-5-(trifluoromethyl)pyridine (0.021 mL, 0.17 mmol), cesium carbonate (75 mg, 0.23 mmol), (R)-(−)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (4.6 mg, 0.0083 mmol) and palladium(II) acetate (1.9 mg, 0.0083 mmol) were diluted with DME (1 mL). The reaction was heated to 90° C. and stirred for 5 hours. The reaction was loaded directly onto a biotage 25 cartridge (silica gel), eluting with 5% ethyl acetate/hexanes to 40% ethyl acetate/hexanes to afford methyl 7-(4-((5-(trifluoromethyl)pyridin-2-yl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (9 mg, 11% yield) as a white solid.

Workup

washeluting with 5% ethyl acetate/hexanes to 40% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-2d76715643c4419282c02cd271240b9e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785445B2

Reaction notes

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