Phosphorus trichloride → HCID 136342132, compound
Reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)[CH:22]=4)[NH:17][C:16]=3[OH:30])=[N+:12]([O-])[CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.P(Cl)(Cl)Cl>C(OCC)(=O)C>[N:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)[CH:22]=4)[NH:17][C:16]=3[OH:30])=[N:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-[5-(morpholin-4-ylmethyl)-1-oxidopyridin-2-yl]-5-pyridin-3-yl-1H-indol-2-ol (200 mg, 0.6 mmol) in ethyl acetate (60 mL) was added phosphorus trichloride (0.4 mL). A yellow precipitate was formed and the mixture was refluxed for 3 h, and then diluted with ethyl acetate and washed with an aqueous saturated NaHCO3 solution. The aqueos layer was extracted with two portions of ethyl acetate and one portion of chloroform. The organic- layers were combined, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by preparative HPLC (column: Xterra, 19×300 mm, eluent: water/acetonitrile, (0:100 to 100:0), gradient) affording 6 mg (3% yield) of the title compound as a yellow solid: 1H NMR (DMSO-d6, 400 MHz) δ 10.50 (br s, 1 H), 8.92 (d, J=2 Hz, 1 H), 8.49 (dd, J=4, 1 Hz, 1 H), 8.12-8.06 (m, 1 H), 8.02 (s, 1 H), 7.90-7.71 (m, 1 H), 7.71-7.67 (m, 2 H), 7.43 (dd, J=8, 5 Hz, 1 H), 7.20 (d, J=8 Hz, 1 H), 6.98 (d, J=8 Hz, 1 H), 3.63-3.53 (m, 4 H), 3.40-3.24 (m, 2 H), 2.42-2.34 (m, 4 H); MS (ES) m/z 388 (M++1).