3,5-Dimethylisoxazole-4-boronic acid → HCID 67108903, compound

HRID 2370984Notes

Reaction equation

Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:19][C:20]1[C:24](B(O)O)=[C:23]([CH3:28])[O:22][N:21]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]=2[C:24]2[C:20]([CH3:19])=[N:21][O:22][C:23]=2[CH3:28])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2-bromo-3-(4-methoxyphenyl)-1H-indole (93 mg, 0.31 mmol), 3 mol % tetrakis(triphenylphosphine)palladium and 3,5-dimethylisoxazol-4-ylboronic acid (3 eq) were mixed in 1.5 ml degassed DME under nitrogen. 1.24 ml sodium hydrogen carbonate (1 M) was added drop wise over 5 min. The resulting mixture was stirred at 90° C. for 45 min and then cooled to rt. The solvent was evaporated under nitrogen flow and the residue was taken up in DCM. Filtering through a short plug of silica gave a crude product which was purified again on silica (EtOAc/n-Heptane 1:9-3:7). 40.5 mg 4-(3-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole was obtained as a yellow solid.

Workup

customdegassed DME under nitrogen
addition1.24 ml sodium hydrogen carbonate (1 M) was added drop wise over 5 min
temperaturecooled to rt
customThe solvent was evaporated under nitrogen flow
filtrationFiltering through a short plug of silica
customgave a crude product which
customwas purified again on silica (EtOAc/n-Heptane 1:9-3:7)

Sources & evidence

ORD record: ord-e740e0cd4b8942e6b07ef072d0a16b67
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710243B2

Reaction notes

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