2,3-Dichloropyridine → HCID 12004368, compound

HRID 971230Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[CH2:18][CH2:17][NH:16][CH2:15][C:14]=3[CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.Cl[C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.CN(C)C(=O)C>[Cl:29][C:28]1[C:23]([N:16]2[CH2:17][CH2:18][C:19]3[C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:20])[F:21])=[CH:8][CH:7]=4)=[N:11][CH:12]=[CH:13][C:14]=3[CH2:15]2)=[N:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 150 °C

Procedure

N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2,6-naphthyridin-1-amine (200 mg, 0.68 mmol) was dissolved in a mixture of dioxane/N,N-dimethylacetamide (4:1) (3 mL). To the mixture was added 2,3-dichloropyridine (200 mg, 1.36 mmol) and N,N-diisopropylethylamine (0.24 mL, 1.36 mmol). The mixture was heated at 150° C. in a Personal Chemistry microwave for 16 h. The solvents were removed under vacuum and the residue was dissolved in ethyl acetate and washed with sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give a brown residue. The residue was purified by flash chromatography over silica gel using a gradient of ethyl acetate:hexane (0-100%) to give the desired compound as an off-white powder (76 mg).

Workup

customThe solvents were removed under vacuum
dissolutionthe residue was dissolved in ethyl acetate
washwashed with sat. NaHCO3 and brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated
customto give a brown residue
customThe residue was purified by flash chromatography over silica gel using a gradient of ethyl acetate

Sources & evidence

ORD record: ord-7126394b41d3452eb9937a5c0cb72978
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312330B2

Reaction notes

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