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

HRID 11035Notes

Reaction equation

HRID 11035 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:15]4[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=4)[C:7]4[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1.B(Br)(Br)Br.COC1C=CC2NC3CC(C(OCC4C=CC=CC=4)=O)C4C(=O)NC(=O)C4C=3C=2C=1>>[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=4)[C:7]4[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 25134Boron tribromideHCID 11843004Benzyl 9-methoxy-1,3-dioxo-1,2,3,3a,4,5,6,10c-octahydropyrrolo[3,4-c]carbazole-4-carboxylateHCID 118432889-hydroxy-4-(4-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 104052129-hydroxy-4-(4-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 92%

Procedure

The reaction of 9-hydroxy-4-(4-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione prepared as decribed in example 34 with BBr3 using the procedure described in example 80 of Scheme 2 gave 9-Hydroxy-4-(4-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (24) (I, Ar=4-hydroxyphenyl) in a 92% yield; mp 230° C. (dec). 1H NMR δ [(CD3)2SO] 11.67 (s, 1H), 10.96 (s, 1H), 9.59 (s, 1H), 9.22 (s, 1H), 8.32 (d, J=2.4 Hz, 1H), 7.51 (s, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.41 (d, J=8.6 Hz, 2H), 7.04 (dd, J=8.7, 2.4 Hz, 1H), 6.84 (d, J=8.6 Hz, 2H). FABMS found [M+H]+: 345.0875. C20H13N2O4 requires 345.0875.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-0d320a739e89434084f2648f376f549b
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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