Methyl 3-(6-methyl-1-(pyridin-2-ylsulfonyl)-1H-indol-2-yl)acrylate → methyl 3-(6-methyl-1H-indol-2-yl)propanoate

HRID 589603Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH:20]=[CH:21][C:22]([O:24][CH3:25])=[O:23])[N:8]2S(C2C=CC=CN=2)(=O)=O)=[CH:4][CH:3]=1>CO.CCOC(C)=O>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[NH:8]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 45 (1.86 g, 5.22 mmol) and Mg (2.54 g, 104.4 mmol) in MeOH (40 mL) was stirred at 0° C. for 2 h. The mixture was diluted with EtOAc and filtered through a pad of Celite. The filtrate was washed with a sat. NaHCO3 solution, brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography eluting with a linear gradient ranging from 0 to 10% EtOAc-hexanes to provide 0.69 g (60%) of product 46 as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 2.43 (s, 3H), 2.74 (t, J=7 Hz, 2H), 3.06 (t, J=7 Hz, 2H), 3.71 (s, 3H), 6.17 (m, 1H), 6.90 (d, J=8 Hz, 1H), 7.10 (s, 1H), 7.40 (d, J=8 Hz, 1H), 8.36 (brs, 1H). LC-MS (CI): m/z 218.1 [(M+H)+ C13H15NO2 requires 217.11].

Workup

filtrationfiltered through a pad of Celite
washThe filtrate was washed with a sat. NaHCO3 solution, brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography
washeluting with a linear gradient

Sources & evidence

ORD record: ord-7099fc05ff2f4ce7b200f2df0752162b
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233921B2

Reaction notes

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