Diisopropylethylamine → HCID 86701546, compound

HRID 2173978Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH2:29][OH:30])[C:5]([CH2:21][O:22]C2CCCCO2)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2.C(N(C(C)C)C(C)C)C.[CH3:40][Si:41]([CH2:44][CH2:45][O:46][CH2:47]Cl)([CH3:43])[CH3:42]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:29][O:30][CH2:47][O:46][CH2:45][CH2:44][Si:41]([CH3:43])([CH3:42])[CH3:40])[C:5]([CH2:21][OH:22])=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution (±)-(7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indol-5-yl)methanol (200 mg, 0.466 mmol) and iPr2EtN (0.16 mL, 0.93 mmol) in CH2Cl2 (2 mL) was added SEMCl (0.124 mL, 0.69 mmol), and then the mixture was stirred at 40° C. for 1 hr. The reaction mixture was concentrated (during the concentration, the THP group was partially removed) and then purified by SiO2 column chromatography (heptane/EtOAc=1/0 to 1/3) to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) δ 7.81 (d, J=3.79 Hz, 1H), 7.58 (d, J=8.30 Hz, 2H), 7.32 (d, J=8.30 Hz, 2H), 7.08 (s, 1H), 6.99 (d, J=3.79 Hz, 1H), 4.79 (d, J=5.81 Hz, 2H), 4.68 (s, 2H), 4.67 (s, 2H), 3.54-3.63 (m, 2H), 3.05 (t, J=5.80 Hz, 1H), 2.54 (s, 3H), 2.35 (s, 3H), 0.82-0.96 (m, 2H), 0.01 (s, 9H).

Workup

concentrationThe reaction mixture was concentrated (
concentrationduring the concentration
customthe THP group was partially removed) and
customthen purified by SiO2 column chromatography (heptane/EtOAc=1/0 to 1/3)

Sources & evidence

ORD record: ord-12d661a989424244a5fd6f77497c4191
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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