Triethylamine → HCID 71293463, compound

HRID 570882Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:23])[N:20]([CH3:22])[N:21]=[C:8]2[NH:7][C:6]=1[CH3:24])=[O:4].[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.CCN(CC)CC>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)[N:9]2[C:19](=[O:23])[N:20]([CH3:22])[N:21]=[C:8]2[N:7]([C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([C:26]([F:37])([F:36])[F:25])[CH:32]=2)[C:6]=1[CH3:24])=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

Intermediate 8 (900 mg, 2.77 mmol), 3-trifluoromethylphenylboronic acid (1.05 g, 5.54 mmol), Et3N (925 μL, 6.6 mmol), and copper (II) acetate (1.0 g, 5.54 mmol) were dissolved in DCE (25 mL), and the reaction mixture was stirred at 80° C. for 18 hours. After cooling to RT the reaction mixture was partitioned between DCM and water. The organic layer was separated, washed with water, followed by brine, then dried (MgSO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 3-10% MeOH in DCM and then using HPLC system 1 to yield the title compound as an orange solid (47 mg).

Workup

temperatureAfter cooling to RT the reaction mixture
customwas partitioned between DCM and water
customThe organic layer was separated
washwashed with water
dry with materialdried (MgSO4)
customevaporated in vacuo
customThe resulting residue was purified by silica gel chromatography
washeluting with a gradient of 3-10% MeOH in DCM

Sources & evidence

ORD record: ord-15627c22287a4b538d78c8d686d3efe9
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023855B2

Reaction notes

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