Potassium Carbonate → 3,5-dimethyl-6,7,8,9-tetrahydro-5H-furo[3',2':5,6]pyrido[2,3-d]azepine

HRID 597920Notes

Reaction equation

[CH3:1][C:2]1[C:6]2=[CH:7][C:8]3[CH:14]([CH3:15])[CH2:13][N:12](C(=O)C(F)(F)F)[CH2:11][CH2:10][C:9]=3[N:22]=[C:5]2[O:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:1][C:2]1[C:6]2=[CH:7][C:8]3[CH:14]([CH3:15])[CH2:13][NH:12][CH2:11][CH2:10][C:9]=3[N:22]=[C:5]2[O:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-(allyloxy)-3-iodo-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine (300 mg, 682 μmol), Pd(PPh3)2Cl2 (120 mg, 170 μmol), NaOAc (168 mg, 2.04 mmol) and DMA (20 ml) was heated for 30 min at 125 ° C. The reaction mixture was concentrated in vacuo and purified by column chromatography to give 68.0 mg (32%) of 3,5-dimethyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H -furo[3′,2′:5,6]pyrido[2,3-d]azepine. H-NMR (CDCl3) δ 7.68 (2× s, 1H), 7.46 (2× s, 1H), 4.25-3.25 (m, 7H), 2.24 (2× d, 3H), 1.44 (2×d, 3H) ppm. A mixture of 3,5-dimethyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-furo[3′,2′:5,6]pyrido[2,3-d]azepine (62.0 mg, 199 μmol), K2CO3 (80 mg) and MeOH (6 ml) was heated for 1 h at 60° C. The reaction mixture was concentrated in vacuo and purified by column chromatography to give 19.6 mg (46%) of 3,5-dimethyl-6,7,8,9-tetrahydro-5H-furo[3′,2′:5,6]pyrido[2,3-d]azepine. 1H-NMR (CDCl3) δ 7.69 (s, 1H), 7.47 (d, 1H), 3.63-3.33 (m, 5H), 3.06 (t, 1H), 2.87 (t, 1H), 2.25 (d, 3H), 1.54 (d, 3H) ppm.

Workup

concentrationThe reaction mixture was concentrated in vacuo
custompurified by column chromatography

Sources & evidence

ORD record: ord-2826bd2ccb324d1eaa6567891d895c77
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897595B2

Reaction notes

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