Borane;tetrahydrofuran → HCID 86640693, compound

HRID 2176113Notes

Reaction equation

HRID 2176113 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=O)=[CH:4][CH:3]=1.B.O1CCCC1>O1CCCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:11][C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 86640692HCID 86640692, compound

Product 1

HCID 86640693HCID 86640693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 500 mL reaction flask containing 2-(6-chloropyridin-3-yl)-N-p-tolylacetamide (12 g, 46 mmol; Example 117A) in tetrahydrofuran (200 mL) was treated with 1 M borane-tetrahydrofuran (100 mL, 100 mmol; Aldrich) and then heated to reflux with stirring for 16 hours. After cooling the reaction mixture to room temperature, it was quenched with ethanol, concentrated and purified by flash chromatography (silica gel, hexanes/ethyl acetate, 2:1) to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.19 (s, 3H), 2.89 (t, J=7 Hz, 2H), 3.35 (t, J=7 Hz, 2H), 6.56 (d, J=8 Hz, 2H), 6.93 (d, J=8 Hz, 2H), 7.37 (d, J=8 Hz, 1H), 7.70 (dd, J=8, 2 Hz, 1H), 8.21 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 247 (M+H)+.

Workup

  1. customA 500 mL reaction flask
  2. temperatureheated
  3. temperatureto reflux
  4. customit was quenched with ethanol
  5. concentrationconcentrated
  6. custompurified by flash chromatography (silica gel, hexanes/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-a37dbed38bf24412b918d786fd269eac
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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