Potassium Carbonate → HCID 89676727, compound

HRID 926165Notes

Reaction equation

[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:24]([CH3:25])=[CH:23][C:22]2[C:17](=[CH:18][C:19](Br)=[CH:20][CH:21]=2)[C:16]=1[O:27][S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:35](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1>[C:1]([O:7][CH2:8][C@@H:9]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:15]1[C:24]([CH3:25])=[CH:23][C:22]2[C:17](=[CH:18][C:19]([CH3:35])=[CH:20][CH:21]=2)[C:16]=1[O:27][S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 125 °C

Procedure

To a solution of (S)-2-(7-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyethyl pivalate (825 mg, 1.45 mmol) in 1,4-dioxane (7 mL) was added potassium carbonate (601 mg, 4.35 mmol), trimethylboroxine (220 mg, 1.74 mmol), and PdXPhos catalyst (107 mg, 0.145 mmol). The mixture was heated in a sealed vial in the microwave at 125° C. for 1 h. The mixture was filtered and concentrated in vacuo. The crude material was purified by column chromatography (EtOAc/hexanes) to give the desired product. 1H-NMR: 400 MHz, (CDCl3) δ: 7.84 (s, 1H), 7.66 (d, J=8 Hz, 1H), 7.62 (s, 1H), 7.36 (d, J=8 Hz, 1H), 5.48 (dd, J=9, 3 Hz, 1H), 4.65 (dd, J=12, 9 Hz, 1H), 4.16 (dd, J=12, 3 Hz, 1H), 2.75 (s, 3H), 2.54 (s, 3H), 1.23 (s, 9H) 1.12 (s, 9H).

Workup

filtrationThe mixture was filtered
concentrationconcentrated in vacuo
customThe crude material was purified by column chromatography (EtOAc/hexanes)

Sources & evidence

ORD record: ord-3710e02c7ecc4640884342a1ae902af5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284323B2

Reaction notes

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