Tetrahydrofuran → HCID 86678964, compound
Reaction equation
I[C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[C:7]([C:9]([C:17]#[N:18])=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:8].[CH2:19]1COCC1>>[C:7]([CH:9]([C:17]#[N:18])[C:10]([CH3:16])([C:2]1[CH:3]=[N:4][N:5]([CH3:19])[CH:6]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:8]Participants
Conditions
- Temperature
- -30 °C
Procedure
Isopropylmagnesium chloride LiCl complex (1627 μl, 2.115 mmol, 1.3 M in THF) was added to a THF solution of 4-iodo pyrazole (400 mg, 1.923 mmol) cooled to −30° C. The reaction was stirred for hours with the temperature maintained between −20 and −30° C. After two hours, ethyl 3,3-dicyano-2-methylprop-2-enoate (1442 μl, 1.442 mmol, 1 M solution in benzene) was quickly added and the reaction was warmed to room temperature and stirred for five minutes. The reaction was then quenched with saturated aqueous NH4Cl and extracted between EtOAc. The organic layer was dried (sodium sulfate) and concentrated in vacuo. Purification by silica gel column chromatography using a hexanes/EtOAc gradient afforded the title product as a clear oil, 1H NMR (500 MHz, CHCl3-d): δ 7.44 (s, 1H); 7.42 (s, 1H); 4.44 (s, 1H); 4.28-4.19 (m, 2H); 3.86 (s, 3H); 1.84 (s, 3H); 1.25 (t, J=7.12 Hz, 3H).
Workup
- temperaturemaintained between −20 and −30° C
- temperaturethe reaction was warmed to room temperature
- stirringstirred for five minutes
- customThe reaction was then quenched with saturated aqueous NH4Cl
- extractionextracted between EtOAc
- dry with materialThe organic layer was dried (sodium sulfate)
- concentrationconcentrated in vacuo
- customPurification by silica gel column chromatography
Sources & evidence
- ORD record
- ord-71b14393844d49af9d102cf9cf87920d
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365574B2
Reaction notes
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