N,N-Diethylethanamine trihydrofluoride → HCID 22285138, compound

HRID 431175Notes

Reaction equation

HRID 431175 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]([C:25]1[C:26]([Cl:35])=[N:27][C:28]3[C:33]([CH:34]=1)=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:12]2)(C(C)(C)C)(C)C.F.F.F.C(N(CC)CC)C>C(#N)C>[Cl:35][C:26]1[C:25]([C:13]2[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:15]3[C:11]([CH:12]=2)=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=3)=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1

Participants

4

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 17930066tert-butyl 5-{[tert-butyl(dimethyl)silyl]oxy}-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate

Product 1

HCID 22285138HCID 22285138, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl 5-{[tert-butyl(dimethyl)silyl]oxy }-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate (1-7, 2.50 g, 4.91 mmol, 1 equiv) and triethylamine trihydrofluoride (3.60 mL, 22.1 mmol, 4.50 equiv) in acetonitrile (100 mL) was stirred at 23° C. for 20 hours. The reaction mixture was concentrated, and the residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated to tert-butyl 2-(2-chloro-3-quinolinyl)-5-hydroxy-1H-indole-1-carboxylate (1-8) as a tan colored foam (2.1 g, 100%). 1H NMR (400 MHz, CDCl3) δ 8.18 (d, 1H, J=9.0 Hz), 8.17 (s, 1H), 8.07 (d, 1H, J=8.4 Hz), 7.86 (d, 1H, J=8.1 Hz), 7.77 (br t, 1H, J=8.4 Hz), 7.61 (br t, 1H, J=8.1 Hz), 7.03 (d, 1H, J=2.6 Hz), 6.93 (dd, 1H, J=8.8, 2.6 Hz), 6.55 (s, 1H), 1.26 (s, 9H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to tert-butyl 2-(2-chloro-3-quinolinyl)-5-hydroxy-1H-indole-1-carboxylate (1-8) as a tan colored foam (2.1 g, 100%)

Sources & evidence

ORD record
ord-ac128ccd826841d6a49445d6b9388779
Source dataset
uspto-grants-2003_12
Patent number
US06656942B2

Reaction notes

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