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

HRID 11036Notes

Reaction equation

HRID 11036 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][CH:18]=[C:17]([O:21]C)[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][CH:18]=[C:17]([OH:21])[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 11843147HCID 11843147, compound

Product 1

HCID 118447519-hydroxy-4-(3-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 88%

Procedure

9-Hydroxy-4-(3-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (prepared as decribed in example 35) was reacted with BBr3 using the procedure described in the proceedure described in example 80 of Scheme 2 to give 9-hydroxy-4-(3-hydroxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (25) (I, Ar=3-hydroxyphenyl) in a yield of 88%; mp 282–285° C. (dec). 1H NMR δ [(CD3)2SO] 11.73 (br s, 1H), 11.00 (br s, 1H), 9.48 (br s, 1H), 9.24 (s, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.54 (s, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.24 (dd, J=7.7, 7.7 Hz, 1H), 7.05 (dd, J=8.7, 2.4 Hz, 1H), 7.01–6.96 (m, 2H), 6.82 (dd, J=8.2, 2.1 Hz, 1H). FABMS found [M+H]+: 345.0865. C20H13N2O4 requires 345.0875.

Sources & evidence

ORD record
ord-b68b64895da645b296feebd4e1aed28a
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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