Tetrabutylammonium Fluoride → 2-{1-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]-1H-indol-2-yl}ethanol

HRID 1092425Notes

Reaction equation

HRID 1092425 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[N:12]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:22][CH:21]=2)[C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[N:30]1([CH2:29][CH2:28][CH2:27][O:26][C:23]2[CH:22]=[CH:21][C:20]([N:12]3[C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:19]=[C:11]3[CH2:10][CH2:9][OH:8])=[CH:25][CH:24]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 576757382-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-1H-indole

Product 1

HCID 166602022-{1-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]-1H-indol-2-yl}ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-1H-indole (0.4 mmol) was dissolved in tetrahydrofuran (2 mL) under N2, and tetrabutylammonium fluoride (0.44 mL, 1 M in tetrahydrofuran, 0.44 mmol) was added. The reaction was stirred at room temperature for 3 hours, then quenched with saturated ammonium chloride. The mixture was diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic extracts were dried over MgSO4 and concentrated. The residue was purified by semi-prep LC-MS to give the desired product, 15.8 mg. LC-MS (C23H28N2O2 calc'd 364) m/z 365 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.61-7.59 (m, 1H), 7.24-7.20 (m, 2H), 7.13-7.07 (m, 2H), 7.03-7.00 (m, 3H), 6.48 (s, 1H), 4.09 (t, J=6.3 Hz, 2H), 3.75 (t, J=6.6 Hz, 2H), 2.89 (t, J=6.6 Hz, 2H), 2.66 (t, J=7.5 Hz, 2H), 2.60-2.49 (m, 4H), 2.10-2.01 (m, 2H), 1.85-1.76 (m, 4H).

Workup

  1. customquenched with saturated ammonium chloride
  2. additionThe mixture was diluted with saturated sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by semi-prep LC-MS

Sources & evidence

ORD record
ord-bc6a36ed31e547f187861d14bb31af43
Source dataset
uspto-grants-2012_03
Patent number
US08129424B2

Reaction notes

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