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

HRID 2264705Notes

Reaction equation

HRID 2264705 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) d 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-d0724eb481024d44aee900ea41ae1b36
Source dataset
uspto-grants-2010_12
Patent number
US07855224B2

Reaction notes

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