Hydrochloric Acid → HCID 53232877, compound

HRID 1891498Notes

Reaction equation

HRID 1891498 reaction equation
[Si]([O:8][CH:9]1[C:17]2[C:12](=[C:13]([C:18]3[S:22][C:21]([C:23]4[CH:24]=[CH:25][C:26]([O:31][CH:32]([CH3:34])[CH3:33])=[C:27]([CH:30]=4)[C:28]#[N:29])=[CH:20][CH:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.Cl>O1CCOCC1>[OH:8][CH:9]1[C:17]2[C:12](=[C:13]([C:18]3[S:22][C:21]([C:23]4[CH:24]=[CH:25][C:26]([O:31][CH:32]([CH3:34])[CH3:33])=[C:27]([CH:30]=4)[C:28]#[N:29])=[CH:20][CH:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58367250HCID 58367250, compound

Product 1

HCID 53232877HCID 53232877, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of 5-(5-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-inden-4-yl)thiophen-2-yl)-2-isopropoxybenzonitrile (80 mg, 0.16 mmol) in 1,4-dioxane (1 mL) was added 4N HCl solution in 1,4-dioxane (1 mL). The reaction mixture was stirred at room temperature for 2 h. Solvent was evaporated and the crude product was purified by chromatography (EA/hexanes) to afford 26 mg (40%) of 5-(5-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)thiophen-2-yl)-2-isopropoxybenzonitrile 223 as a white solid. LCMS-ESI (m/z) calculated for C23H21NO2S: 375.1; found 398.1 [M+Na]+, tR=3.96 min. 1H NMR (400 MHz, CDCl3) δ 7.77 (d, J=2.3 Hz, 1H), 7.71 (dd, J=8.8, 2.4 Hz, 1H), 7.53-7.45 (m, 1H), 7.38 (d, J=7.4 Hz, 1H), 7.30 (t, J=7.5 Hz, 1H), 7.19 (q, J=3.8 Hz, 2H), 6.97 (d, J=8.9 Hz, 1H), 5.28 (t, J=6.1 Hz, 1H), 4.66 (dt, J=12.2, 6.1 Hz, 1H), 3.28 (ddd, J=16.2, 8.5, 4.7 Hz, 1H), 3.11-2.91 (m, 1H), 2.53 (dddd, J=13.1, 8.2, 6.9, 4.7 Hz, 1H), 2.08-1.92 (m, 1H), 1.57 (s, 1H), 1.41 (d, J=6.1 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ 159.37, 146.65, 142.74, 141.52, 140.36, 131.55, 131.08, 130.96, 130.79, 127.79, 127.54, 126.67, 123.82, 116.57, 114.40, 103.82, 76.59, 72.43, 36.07, 30.88, 22.08.

Workup

  1. customSolvent was evaporated
  2. customthe crude product was purified by chromatography (EA/hexanes)

Sources & evidence

ORD record
ord-5be21c60eddb4b93982d62f08ebf0f8a
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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