Potassium Carbonate → HCID 67778655, compound

HRID 1026360Notes

Reaction equation

Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[OH:6][C:7]1[CH:30]=[CH:29][C:10]2[CH2:11][C:12]([C:15]3[N:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]([NH:25][C:26](=[O:28])[CH3:27])[CH3:24])=[CH:17][CH:16]=3)([CH3:14])[O:13][C:9]=2[CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:5]1([CH2:4][O:6][C:7]2[CH:30]=[CH:29][C:10]3[CH2:11][C:12]([C:15]4[N:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]([NH:25][C:26](=[O:28])[CH3:27])[CH3:24])=[CH:17][CH:16]=4)([CH3:14])[O:13][C:9]=3[CH:8]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (bromomethyl)cyclopropane (177 mg), diastereomer of N-[(1S)-2-{[6-(6-hydroxy-2-methyl-2,3-dihydro-1-benzofuran-2-yl)pyridin-3-yl]oxy}-1-methylethyl]acetamide (150 mg) and potassium carbonate (72.7 mg) in DMF (3 mL) was stirred at 80° C. for 3 hr. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The separated organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (150 mg).

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated under reduced pressure
customThe residue was partitioned between ethyl acetate and water
washThe separated organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record: ord-3d09669a70184515aec115bcb16b338e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729102B2

Reaction notes

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