Water → HCID 71009214, compound

HRID 1527245Notes

Reaction equation

C([Si](C(C)C)(C(C)C)[N:5]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)(C)C.C1COCC1.O.C([O-])([O-])=O.[K+].[K+]>CCO>[CH:23]([Si:16]([CH:17]([CH3:19])[CH3:18])([CH:20]([CH3:22])[CH3:21])[O:15][CH2:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[NH:5][CH:6]=[CH:7]2)([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of 1-triisopropylsilanyl-5-triisopropylsilanyloxymethyl-1H-indole (2.80 g, 6.09 mmol) in EtOH (30 mL)/THF (10 mL)/water (10 mL) was added K2CO3 (4.21 g, 30.4 mmol), and the reaction mixture was heated at 85° C. for 16 h. The reaction was quenched with 1N HCl at 0° C. The aqueous layer was extracted with CH2Cl2 (2×) and the combined organic layers were washed with brine, dried (phase separator) and concentrated under reduced pressure. The oily residue was purified by flash column chromatography on silica gel (eluent gradient: c-hexane to c-hexane/EtOAc 9:1) to afford the title compound as a yellow oil. TLC, Rf (c-hexane/EtOAc 9:1)=0.29. tR (HPLC conditions k): 5.02 min. MS (LC/MS): 304 [M+H]+.

Workup

customThe reaction was quenched with 1N HCl at 0° C
extractionThe aqueous layer was extracted with CH2Cl2 (2×)
washthe combined organic layers were washed with brine
customdried (phase separator)
concentrationconcentrated under reduced pressure
customThe oily residue was purified by flash column chromatography on silica gel (eluent gradient: c-hexane to c-hexane/EtOAc 9:1)

Sources & evidence

ORD record: ord-d2747c3e9f5f425aadf8012097b6d2c6
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085555B2

Reaction notes

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