Potassium Carbonate → HCID 66759657, compound

HRID 2063828Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O.[Br:23][C:24]1[C:25]([CH3:38])=[C:26]([CH3:37])[C:27]2[O:31][C:30]([CH2:33]I)([CH3:32])[CH2:29][C:28]=2[C:35]=1[CH3:36]>C(OCC)(=O)C.O>[Br:23][C:24]1[C:25]([CH3:38])=[C:26]([CH3:37])[C:27]2[O:31][C:30]([CH2:32][N:8]3[CH2:9][CH2:10][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:6][CH2:7]3)([CH3:33])[CH2:29][C:28]=2[C:35]=1[CH3:36]

Participants

Conditions

Temperature: 200 °C

Procedure

1,4-dioxa-8-azaspiro[4.5]decane (725 mg, 5.06 mmol) and potassium carbonate (699 mg, 5.06 mmol) were added to a solution of DMA (3 mL) containing 5-bromo-2-(iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran (400 mg, 1.01 mmol) synthesized in Reference Example 133, and the mixture was stirred under microwave irradiation at 200° C. for 10 minutes. The reaction solution was cooled to room temperature, and water and ethyl acetate were added thereto to separate an organic layer. The organic layer was washed with water and saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-80:20) to give 310 mg of the title compound (yield: 75%).

Workup

customsynthesized in Reference Example 133
temperatureThe reaction solution was cooled to room temperature
customto separate an organic layer
washThe organic layer was washed with water and saturated saline
customdried
concentrationfollowed by concentration under reduced pressure
customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-80:20)

Sources & evidence

ORD record: ord-944b37f223074ce5be553cac19c362ef
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288390B2

Reaction notes

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