Morpholine → HCID 50994270, compound

HRID 1784861Notes

Reaction equation

HRID 1784861 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:15]=[C:14]([Br:16])[CH:13]=[C:12]([Br:17])[CH:11]=2)=[O:9])[CH:5]=[CH:4][N:3]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>O1CCOCC1>[Br:17][C:12]1[CH:11]=[C:10]([C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:7]=2)=[O:9])[CH:15]=[C:14]([Br:16])[CH:13]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 50994269HCID 50994269, compound

Product 1

HCID 50994270HCID 50994270, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To (2-chloro-pyridin-4-yl)-(3,5-dibromo-phenyl)-methanone (0.200 g, 0.53 mmol) in 1.0 mL of 1,4-dioxane in a microwave tube was added 0.070 g (0.80 mmol) morpholine. The reaction was subjected to microwave irradiation at 120° C. for 60 minutes. The reaction mixture was cooled and concentrated. The crude product was chromatographed on silica gel using 1:1 hexane:ethyl acetate to give 0.118 g of the (3,5-dibromo-phenyl)-(2-morpholin-4-yl-pyridin-4-yl)-methanone. This compound was converted to [3-(1H-indol-4-yl)-5-(2-morpholin-4-yl-pyridine-4-carbonyl)-phenyl]-carbamic acid methyl ester as described for Example 90. 1H NMR (400 MHz, CDCl3): δ 8.28 (d, J=5.3 Hz, 1H), 8.07 (t, J=1.8 Hz, 1H), 7.95 (s, 1H), 7.76 (t, J=1.6 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.29 (d, J=3.3 Hz, 1H), 7.18 (t, J=7.7 Hz, 1H), 7.10 (d, J=7.4 Hz, 1H), 7.08 (s, 1H), 6.95 (dd, J=5.1, 1.0 Hz, 1H), 6.62 (d, J=3.1 Hz, 1H), 3.78 (t, J=4.9 Hz, 4H), 3.75 (s, 3H), 3.54 (t, J=4.9 Hz, 4H).

Workup

  1. customirradiation at 120° C. for 60 minutes
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel using 1:1 hexane

Sources & evidence

ORD record
ord-90586a893ad24e0db7054077ceb13cb3
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

Loading…