Hydrochloric Acid → HCID 76798884, compound

HRID 1254123Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:21][C:22]1[N:27]=[CH:26][C:25]2[C:28](=O)[O:29][CH:30]([CH2:31][CH3:32])[C:24]=2[CH:23]=1.Cl>C1COCC1>[Cl:21][C:22]1[N:27]=[CH:26][C:25]2[C:28](=[C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][C:2]3=[O:10])[O:29][CH:30]([CH2:31][CH3:32])[C:24]=2[CH:23]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of 1,3-dihydro-indol-2-one (650 mg, 4.77 mmol.) in THF (10 mL) is cooled to 0° C. under an argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (9.6 mL of a 1 M solution in THF, 9.6 mmol) dropwise. The ice bath is removed and 6-chloro-1-ethyl-1H-furo[3,4-c]pyridin-3-one (630 mg, 3.18 mmol) is added directly as a solid. The resulting solution is stirred for 4.5 h. The reaction mixture is poured into aqueous 10% HCl solution (100 mL) and stirred at room temperature for 10 min and then heated at 90-100° C. for 2 h. The reaction mixture is cooled to room temperature for 36 h during which time a precipitate formed. The precipitate which formed is collected by filtration and dried to give the title compound as an orange solid (670 mg, 67%).

Workup

customThe ice bath is removed
stirringstirred at room temperature for 10 min
temperatureThe reaction mixture is cooled to room temperature for 36 h during which time a precipitate
customformed
customThe precipitate which formed
filtrationis collected by filtration
customdried

Sources & evidence

ORD record: ord-777e67875b27403c9f6fd757fac22164
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455535B2

Reaction notes

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