N,N-Dimethylaniline → 8-Chloro-5-(3-ethanesulfonyl-phenyl)-3-methyl-9H-dipyrido[2,3-b; 4',3'-d]pyrrole
Reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[C:17]3[C:18]4[CH:24]=[C:23]([CH3:25])[CH:22]=[N:21][C:19]=4[NH:20][C:16]=3[C:15](=O)[NH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:38]>>[Cl:38][C:15]1[C:16]2[NH:20][C:19]3[N:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:18]=3[C:17]=2[C:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:7]=2)=[CH:13][N:14]=1Participants
4
Procedure
Compound 31 (50 mg, 0.136 mmol) stirred in POCl3 (2 mL) with dimethylaniline (0.1 mL) at 108° C. under nitrogen for 16 h. The solution was concentrated and dissolved in CH2Cl2. Ice and saturated NaHCO3 solution were added, and organics were extracted (2×) with CH2Cl2, dried (MgSO4), and concentrated in vacuo. Purification by silica gel chromatography (3% MeOH/CH2Cl2) gave 36 mg (69%) of the title compound as a pale yellow solid. 1H NMR (400 MHz, MeOD-d4/CDCl3): δ 8.46 (s, 1H), 8.22 (s, 1H), 8.14 (s, 1H), 8.11 (d, 1H, J=8.0 Hz), 8.01 (d, 1H, J=8.0 Hz), 7.89 (t, 1H, J=8.0 Hz), 7.84 (s, 1H), 7.76 (s, 1H), 3.28 (q, 2H, J=7.2 Hz), 2.38 (s, 3H), 1.31 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C19H16ClN3O2S, 386, 388; found 386, 388.
Workup
- concentrationThe solution was concentrated
- dissolutiondissolved in CH2Cl2
- additionIce and saturated NaHCO3 solution were added
- extractionorganics were extracted (2×) with CH2Cl2
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customPurification by silica gel chromatography (3% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-d02def16214c4db1b33e57096b485dc1
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318939B2
Reaction notes
Loading…