Potassium Carbonate → HCID 67126072, compound

HRID 514047Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:30])[C:6]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:7]2[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.[CH3:31]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:26]([O:25][CH:19]([C:6]1[C:5]([CH3:30])=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[CH3:31])[C:7]=1[C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH3:28])([CH3:27])[CH3:29]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 2-(5-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate (100 mg, 0.204 mmol) and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.086 mL, 0.61 mmol) in toluene:ethanol (2:1, 3 mL) and water (1 mL) was added potassium carbonate (282 mg, 2.04 mmol) and PdCl2(dppf) (15 mg, 0.02 mmol) and the reaction was degassed with argon for 10 minutes. The reaction was heated to 100° C. for 20 minutes in a microwave reactor. The crude reaction was purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a yellow oil (32 mg) 1H-NMR: 400 MHz, (CD3OD) δ: 8.08-7.87 (m, 2H), 7.87 (s, 1H), 7.65-7.35 (m, 1H), 7.26 (m, 2H), 7.15 (d, J=7.2 Hz, 1H), 7.09 (d, J=8.0 Hz, 1H). 5.10 (s, 1H), 4.14 (m, 2H), 2.69 (s, 3H), 2.65 (s, 3H), 1.20 (t, J=6.8 Hz, 3H), 0.99 (s, 9H).

Workup

customthe reaction was degassed with argon for 10 minutes
customThe crude reaction
customwas purified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-f58c6b496f5f4f5f99b31492c34d67d0
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102614B2

Reaction notes

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