N,N-Diethylethanamine trihydrofluoride → HCID 22668358, compound

HRID 381768Notes

Reaction equation

HRID 381768 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:14]([C:26]1[C:27]([Cl:36])=[N:28][C:29]3[C:34]([CH:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:13]2)(C(C)(C)C)(C)C.F.F.F.C(N(CC)CC)C>C(#N)C>[Cl:36][C:27]1[C:26]([C:14]2[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:16]3[C:12]([CH:13]=2)=[CH:11][C:10]([CH2:9][OH:8])=[CH:18][CH:17]=3)=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1

Participants

4

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 17930092HCID 17930092, compound

Product 1

HCID 22668358HCID 22668358, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate (7-1, 2.50 g, 4.78 mmol, 1 equiv) and triethylamine trihydrofluoride (3.89 mL, 23.9 mmol, 5.00 equiv) in acetonitrile (100 mL) was heated at 50° C. for 3 h. The reaction mixture was carefully partitioned between saturated sodium bicarbonate solution and ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate and concentrated to give tert-butyl 2-(2-chloro-3-quinolinyl)-5-(hydroxymethyl)-1H-indole-1-carboxylate (7-2) as a tan foam. 1H NMR (500 MHz, CDCl3) δ8.31 (d, 1H, J=8.5 Hz), 8.19 (s, 1H), 8.08 (d, 1H, J=8.5 Hz), 7.87 (d, 1H, J=8.1 Hz), 7.78 (br t, 1H, J=8.0 Hz), 7.63 (s, 1H), 7.62 (br t, 1H, J=8.0 Hz), 7.41 (d, 1H, J=8.5 Hz), 6.66 (s, 1H ), 4.82 (d, 2H, J=4.9 Hz), 1.81 (br s, 1H), 1.27 (s, 9H).

Workup

  1. customThe reaction mixture was carefully partitioned between saturated sodium bicarbonate solution and ethyl acetate (2×100 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c8c2c098cd404727a631ecf2ec6525cd
Source dataset
uspto-grants-2001_10
Patent number
US06306874B1

Reaction notes

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