Potassium Iodide → HCID 66599453, compound

HRID 2410842Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12]Cl)[N:6]=[CH:5]2.[I-].[K+].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[N:6]=[CH:5]2

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5-bromo-1-(2-chloroethyl)-1H-indazole (500 mg, 1.93 mmol), potassium iodide (1.28 mg, 7.71 mmol) and morpholine (1.0 mL, 12 mmol) in NMP (3 mL) in a sealed vial was heated at 70° C. overnight. Preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, elution gradient of 0 to 60% B over 20 min at 42 mL/min) afforded 4-(2-(5-bromo-1H-indazol-1-yl)ethyl)morpholine (549 mg, 1.77 mmol, 92% yield) as a solid. MS (ESI) m/z 311.98 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 7.89 (1H, s), 7.81 (1H, s), 7.38-7.42 (1H, m), 7.29 (1H, d, J=8.85 Hz), 4.44 (2H, t, J=6.87 Hz), 3.58-3.63 (4H, m), 2.82 (2H, t, J=6.87 Hz), 2.41-2.48 (4H, m).

Workup

washPreparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, elution gradient of 0 to 60% B over 20 min at 42 mL/min)

Sources & evidence

ORD record: ord-3120cbe1884f462ba0afe345d810a9b2
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

Loading…