Hydrochloric Acid → 4-[4-(cyclopropylsulfonyl)-1H-indazol-1-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

HRID 1802885Notes

Reaction equation

[CH:1]1([S:4]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[N:10][N:11]3[CH:16]([CH2:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:17](N(OC)C)=[O:18])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH:30]([Mg]Br)=[CH2:31].Cl>O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[N:10][N:11]3[CH:16]([CH2:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:17](=[O:18])[CH:30]=[CH2:31])(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-[4-(cyclopropylsulfonyl)-1H-indazol-1-yl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (2.30 g) in tetrahydrofuran (20 ml) was slowly added vinylmagnesium bromide (1.0M tetrahydrofuran solution: 16.4 mL) at 0° C., and the mixture was stirred at 0° C. for 20 min. The reaction mixture was poured into an ice-cooled 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to give the title compound (1.80 g, yield 84%) as a colorless oil from the fraction eluted with ethyl acetate-hexane (3:1, volume ratio). MS: 389 (MH+).

Workup

customat 0° C.
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-1a67ca61bd2a4751b2dfa1984c4f3a0f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349886B2

Reaction notes

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