Potassium Carbonate → HCID 54591943, compound

HRID 2276758Notes

Reaction equation

Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:21])([CH3:20])[CH2:18][NH2:19])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([CH3:21])([CH3:20])[CH2:18][NH:19][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 6-chloronicotinonitrile (200 mg, 1.46 mmol, 1.0 equiv) and 2-(4-fluorophenyl)-2-methylpropan-1-amine (290 mg, 1.75 mmol, 1.2 equiv) in isopropanol (3 mL) in a microwave vial equipped with a stir bar was added potassium carbonate (720 mg, 2.19 mmol, 1.5 equiv). The vial was fitted with a microwave vial cap and heated to 120° C. for 20 min. The reaction mixture was filtered to remove the solid potassium carbonate and concentrated in vacuo. After the residue was redissolved in EtOAc and water, the organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (1%-3% MeOH/DCM) provided the title compound as a beige solid (104 g, 27%), (m/z [M+H]=270.1).

Workup

customThe vial was fitted with a microwave
customvial cap
filtrationThe reaction mixture was filtered
customto remove the solid potassium carbonate
concentrationconcentrated in vacuo
dissolutionAfter the residue was redissolved in EtOAc
washwater, the organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customPurification by silica gel chromatography (1%-3% MeOH/DCM)

Sources & evidence

ORD record: ord-adc7270409314b589620b03e3a17d909
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133123B2

Reaction notes

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