2-Ethylphenylboronic Acid (contains varying amounts of Anhydride) → HCID 11842998, compound

HRID 11027

Reaction equation

HRID 11027 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8](I)[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1.[CH2:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O)[CH3:22]>>[CH2:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:8]1[C:7]2[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=2[C:5]2[C:4]3[CH:3]=[C:2]([OH:1])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1)[CH3:22]

Participants

3

Reactant 2

HCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 11842998HCID 11842998, compoundYield 69%

Procedure

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-ethylbenzeneboronic acid according to the procedure described in example 8 gave 4-(2-Ethylphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (501) (I; Ar=2-ethylphenyl) in a 69% yield; mp (MeOH/CH2Cl2/hexane) 273–275° C. 1H NMR [(CD3)2SO] δ 11.73 (br s, 1H), 10.95 (br s, 1H), 9.25 (s, 1H), 8.32 (d, J=2.4 Hz, 1H), 7.44 (s, 1H), 7.44 (d, J=8.6 Hz, 1H), 7.36 (td, J=7.2, 1.5 Hz, 1H), 7.33 (dd, J=8.1, 2.2 Hz, 1H), 7.25 (td, J=7.0, 1.8 Hz, 1H), 7.20 (dd, J=7.5, 1.2 Hz, 1H), 7.07 (dd, J=8.7, 2.5 Hz, 1H), 2.42 (m, 2H), 0.96 (t, J=7.6 Hz, 3H). Found: C, 73.83; H, 4.46; N, 7.82. C22H16N2O3 requires C, 74.15; H, 4.53; N, 7.86.

Sources & evidence

ORD record
ord-3d557bcc8372498786e80538b61d2742
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

Loading…