Tetrabutylammonium Fluoride → 1-[5-Chloro-2-(trifluoromethyl)benzyl]-7-(1H-pyrrol-3-yl)-1,2,3,4-tetrahydro-pyrido[2,3-b]pyrazine

HRID 659446Notes

Reaction equation

HRID 659446 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:52]([F:55])([F:54])[F:53])=[C:24]([CH:51]=1)[CH2:25][N:26]1[CH2:31][CH2:30][NH:29][C:28]2[N:32]=[CH:33][C:34]([C:36]3[CH:40]=[CH:39][N:38]([Si](C(C)C)(C(C)C)C(C)C)[CH:37]=3)=[CH:35][C:27]1=2>O1CCCC1>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:52]([F:55])([F:53])[F:54])=[C:24]([CH:51]=1)[CH2:25][N:26]1[CH2:31][CH2:30][NH:29][C:28]2[N:32]=[CH:33][C:34]([C:36]3[CH:40]=[CH:39][NH:38][CH:37]=3)=[CH:35][C:27]1=2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57885999HCID 57885999, compound

Product 1

HCID 578860301-[5-Chloro-2-(trifluoromethyl)benzyl]-7-(1H-pyrrol-3-yl)-1,2,3,4-tetrahydro-pyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous tetrahydrofuran (1 mL) and tetrabutylammonium fluoride, 1 M solution in tetrahydrofuran (0.761 mL) were added to 1-[5-chloro-2-(trifluoromethyl)benzyl]-7-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-1,2,3,4-tetrahydro-pyrido[2,3-b]pyrazine (107 mg, 0.000195 mol). The reaction was stirred at room temperature under nitrogen for two (2) hours and then concentrated. The residue was purified on normal phase silica gel chromatography to give the title compound as an off-white solid. LCMS: m/z=393.24 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.35 (2H, bs), 3.48 (2H, m), 3.63 (2H, m), 4.59 (2H, s), 6.26 (1H, s), 6.56 (1H, d, J=1.3 Hz), 6.74 (1H, t, J=2.0 Hz), 6.82 (1H, s), 7.34 (1H, d, J=8.3 Hz), 7.50 (1H, s), 7.60 (1H, s), 7.64 (1H, d, J=8.3 Hz).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified on normal phase silica gel chromatography

Sources & evidence

ORD record
ord-bb82048ce62746cc9f97eeb8091965fe
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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