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

HRID 2074667Notes

Reaction equation

HRID 2074667 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 578859991-[5-Chloro-2-(trifluoromethyl)benzyl]-7-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

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-82789b3132d744c394b01b51d39651fb
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

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