1,2-Dichlorobenzene → HCID 66605654, compound

HRID 2410725Notes

Reaction equation

HRID 2410725 reaction equation
[N:1]([C:4]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21]C3C=CC=CC=3)=[CH:16][CH:15]=2)=[N:12][C:11]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[N+]=[N-].Cl[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1Cl>>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]2[C:13]3[N:12]=[C:11]([C:28]4[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=4)[CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]=3[NH:1][C:15]=2[CH:16]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 86663012HCID 86663012, compound

Product 1

HCID 66605654HCID 66605654, compound

Procedure

A solution of methyl 3-azido-2-(4-(benzyloxy)phenyl)-6-(4-methoxyphenyl)isonicotinate (Example 205C, 356 mg, 0.763 mmol) in 1,2-dichlorobenzene (10 mL) was heated at 165° C. for 20 min. The solvent was removed under a stream of nitrogen to leave crude methyl 7-(benzyloxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate as a yellow solid: 1H NMR (CDCl3) δ ppm 9.37 (1H, s), 8.29 (1H, d, J=8.85 Hz), 8.13 (1H, s), 8.07-8.12 (2H, m), 7.47-7.51 (2H, m), 7.38-7.44 (2H, m), 7.31-7.37 (1H, m), 7.00-7.05 (3H, m), 5.19 (2H, s), 4.07 (3H, s), 3.88 (3H, s). This was suspended in a solution of 7 N ammonia in methanol (12 mL) and heated in a sealed microwave vial at 60° C. for 36 hr. The solvent was removed and the residue was dissolved in methylene chloride. An equal volume of hexane was added and the precipitate was collected by filtration. This gave 160 mg of 7-(benzyloxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide as a yellow solid. MS (ESI) m/z 424.1 (M+H). 1H NMR (DMSO-d6) δ ppm 11.38 (1H, s), 8.55 (1H, br. s.), 8.28 (1H, s), 8.23 (2H, d, J=8.85 Hz), 8.12 (1H, d, J=8.55 Hz), 7.83 (1H, br. s.), 7.49-7.57 (2H, m), 7.44 (2H, t, J=7.48 Hz), 7.31-7.40 (2H, m), 7.10 (2H, d, J=8.85 Hz), 6.97 (1H, dd, J=8.70, 2.29 Hz), 5.22 (2H, s), 3.85 (3H, s).

Workup

  1. customThe solvent was removed under a stream of nitrogen

Sources & evidence

ORD record
ord-5ad79709458e4a508120b1626e3e46cd
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…