Aniline → HCID 12192484, compound

HRID 2117964Notes

Reaction equation

HRID 2117964 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[C:5]2=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=3)[O:9][C:10](=O)[C:4]2=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1CCC(N=C=NC2CCCCC2)CC1>FC(F)(F)C(O)=O.C(Cl)Cl>[CH3:1][N:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]2[C:5](=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=3)[N:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:10]2=[O:9])[C:6]1=[O:7]

Participants

6

Reactant 3

HCID 6115AnilineHCID 10868DicyclohexylcarbodiimideHCID 12192481HCID 12192481, compound

Product 1

HCID 12192484HCID 12192484, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of furopyrrole 7 (300 mg, 0.79 mmol), aniline (146 mg, 1.57 mmol), DCC (323 mg, 1.57 mmol), trifluoroacetic acid (2-3 drops) and DCM was stirred at room temperature for 144 hours. The solvent was removed, and washing with methanol gave the pyrrolopyrrole 8 as a red solid (173 mg, 55%), m.p. 255-256° C. δH (CDCl3) 7.88-7.83 (2H, m, Ar—H), 7.49-7.43 (5H, m, Ar—H), 7.40-7.26 (5H, m, Ar—H), 7.12-7.07 (2H, m, Ar—H) and 3.35 (3H, s, NCH3)

Workup

  1. customThe solvent was removed
  2. washwashing with methanol

Sources & evidence

ORD record
ord-dce3c53e49a2477b8d11ca16607a8d3c
Source dataset
uspto-grants-2008_10
Patent number
US07442804B2

Reaction notes

Loading…