Potassium Carbonate → HCID 89681748, compound

HRID 926177Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:28])[C:6]([C@H:17]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:7]2[O:12][S:13]([CH3:16])(=[O:15])=[O:14].[CH3:29]B1OB(C)OB(C)O1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCO>[C:24]([O:23][C@@H:17]([C:6]1[C:5]([CH3:28])=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[CH3:29])[C:7]=1[O:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:26])([CH3:27])[CH3:25]

Participants

Conditions

Temperature: 125 °C

Procedure

A solution of (S)-ethyl 2-(5-bromo-3-methyl-1-(methylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate (0.47 g, 0.99 mmol) in toluene/EtOH (6 mL/2.5 mL) was treated with trimethylboroxine (0.42 mL, 3 mmol), PdCl2dppf (0.036 g, 0.05 mmol) and K2CO3 (2M, 1.5 mL, 3 mmol). The vessel was sealed and sparged with Ar for 20 minutes prior to heating in a microwave reactor at 125° C. for 90 minutes. The reaction mixture was loaded directly onto silica gel and purified via Yamazen column chromatography to afford (S)-ethyl 2-tert-butoxy-2-(3,5-dimethyl-1-(methylsulfonyloxy)naphthalen-2-yl)acetate that was approximately an 85:15 mixture with an inseparable, uncharacterized side product. 1H-NMR: 400 MHz, (CDCl3) δ: 8.09 (br d, J=8.4 Hz, 1H); 7.77 (s, 1H); 7.44 (dd, J=8.4, 7.2 Hz, 1H); 7.35 (d, J=7.2 Hz, 1H); 5.77 (s, 1H); 4.27-4.09 (m, 2H); 3.43 (s, 3H); 2.68 (s, 3H); 2.63 (s, 3H); 1.24 (s, 9H); 1.20 (t, J=7.2 Hz, 3H).

Workup

customThe vessel was sealed
customsparged with Ar for 20 minutes
custompurified via Yamazen column chromatography

Sources & evidence

ORD record: ord-9f4a5364782e4071a9bf6a5eff13bd3d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284323B2

Reaction notes

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