Boron tribromide → 5-ethyl-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11146Notes

Reaction equation

HRID 11146 reaction equation
[CH2:1]([C:3]1[C:15]2[NH:14][C:13]3[CH:12]=[CH:11][C:10]([O:16]C)=[CH:9][C:8]=3[C:7]=2[C:6]2[C:18](=[O:22])[NH:19][C:20](=[O:21])[C:5]=2[C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:2].B(Br)(Br)Br>>[CH2:1]([C:3]1[C:15]2[NH:14][C:13]3[CH:12]=[CH:11][C:10]([OH:16])=[CH:9][C:8]=3[C:7]=2[C:6]2[C:18](=[O:22])[NH:19][C:20](=[O:21])[C:5]=2[C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:2]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 118436855-Ethyl-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 118428375-ethyl-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 97%

Procedure

Demethylation of (825) prepared as described in example 423 with BBr3 using the procedure described in example 80 gave (826) (97%), mp 190–196° C. 1H NMR δ [(CD3)2SO] 11.63 (s, 1H), 10.81 (s, 1H), 9.21 (s, 1H), 8.31 (d, J=2.4 Hz, 1H), 7.48–7.40 (m, 4H), 7.31–7.29 (m, 2H), 7.06 (dd, J=8.7, 2.4 Hz, 1H), 2.74 (q, J=7.4 Hz, 2H), 1.06 (t, J=7.4 Hz, 3H). Found: C, 72.43; H, 4.54; N, 7.54. C22H16N2O3.1/2H2O requires: C, 72.32; H, 4.69; N, 7.67.

Sources & evidence

ORD record
ord-c1675234c70240b48ae826e8c683167a
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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