Tetrabutylammonium Fluoride → HCID 58367225, compound

HRID 1891502Notes

Reaction equation

HRID 1891502 reaction equation
[Si]([O:8][CH:9]1[C:17]2[C:12](=[C:13]([C:18]3[CH:19]=[C:20]([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])[S:21][CH:22]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH:9]1[C:17]2[C:12](=[C:13]([C:18]3[CH:19]=[C:20]([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])[S:21][CH:22]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58367162HCID 58367162, compound

Product 1

HCID 58367225HCID 58367225, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Prepared using General Procedure 3. To a solution of 5-(4-(1-((tert-butyldimethylsilyl)oxy)-2,3-dihydro-1H-inden-4-yl)thiophen-2-yl)-2-isopropoxybenzonitrile (17 mg, 0.03 mmol) in THF (1 mL) was added 1M solution of TBAF in tetrahydrofuran (0.3 mL, 0.3 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and purified by preparative HPLC to yield 8 mg (46%) of 5-(4-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)thiophen-2-yl)-2-isopropoxybenzonitrile 226 as white solid. LCMS-ESI (m/z) calculated for C23H21NO2S: 375.1; found 398.1 [M+Na]+. tR=3.84 min; 1H NMR (400 MHz, CDCl3) δ 7.78 (d, J=2.3 Hz, 1H), 7.72 (dd, J=8.8, 2.4 Hz, 1H), 7.43-7.36 (m, 2H), 7.35-7.28 (m, 1H), 7.26 (d, J=1.4 Hz, 1H), 7.24 (s, 1H), 7.06-6.89 (m, 1H), 5.29 (t, J=6.1 Hz, 1H), 4.77-4.49 (m, 1H), 3.20 (ddd, J=16.0, 8.4, 4.7 Hz, 1H), 3.01-2.86 (m, 1H), 2.50 (dddd, J=13.0, 8.1, 6.8, 4.7 Hz, 1H), 2.11-1.88 (m, 1H), 1.58 (s, 1H), 1.41 (d, J=6.1 Hz, 6H); 13 NMR (101 MHz, CDCl3) δ 159.51, 146.35, 142.55, 142.00, 140.88, 133.16, 131.79, 131.24, 128.14, 127.69, 127.56, 124.16, 123.54, 122.06, 116.54, 114.39, 103.84, 76.68, 72.45, 36.28, 30.50, 22.08.

Workup

  1. customPrepared
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b1bdef7d01604a8b8cf227b3ce1b230b
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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