Dimethylformamide → HCID 67959990, compound
Reaction equation
[C:1]12([C:8]3=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=[C:7]3[CH2:6][O:5][CH2:4]1)[CH2:3][CH2:2]2.CN(C)C=O.Cl[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=1>>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([O:13][C:9]2[C:8]3[C:1]4([CH2:4][O:5][CH2:6][C:7]=3[CH:12]=[CH:11][CH:10]=2)[CH2:3][CH2:2]4)=[N:21][CH:22]=1)([O-:28])=[O:27]Participants
Conditions
- Temperature
- 110 °C
Procedure
To a solution of 1H-spiro[2-benzopyran-4,1′-cyclopropan]-5-ol (Intermediate 136, 150 mg) in dry N,N-dimethylformamide (4 ml) potassium carbonate (176 mg, 1.277 mmol) and then 2-chloro-5-nitropyridine (148 mg, 0.936 mmol) were added and the reaction mixture was stirred for 1 h at 110° C. After cooling the reaction was quenched with brine (1 ml), diluted with water (5 ml) and extracted with ethyl acetate (3×15 ml). The organic layer was washed with ice cold brine (2×10 ml), dried over sodium sulphate, filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a 25 g SNAP column and cyclohexane/ethyl acetate as eluents from 100:0 to 7:3. This afforded the title compound as a colourless gum (240 mg).
Workup
- temperatureAfter cooling the reaction
- customwas quenched with brine (1 ml)
- additiondiluted with water (5 ml)
- extractionextracted with ethyl acetate (3×15 ml)
- washThe organic layer was washed with ice cold brine (2×10 ml)
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customevaporated
- customthe residue was purified by flash chromatography (Biotage system) on silica gel using a 25 g SNAP column and cyclohexane/ethyl acetate as eluents from 100:0 to 7:3
Sources & evidence
- ORD record
- ord-733ae27268194225b59ea9ce65f78bab
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346790B2
Reaction notes
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