Boron tribromide → 3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1h)-yl)propanamide

HRID 11110Notes

Reaction equation

HRID 11110 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:26]C)[CH:14]=[CH:13][C:12]=3[N:11]([CH2:28][CH2:29][C:30]([NH2:32])=[O:31])[C:10]=2[CH:9]=1.B(Br)(Br)Br>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:28][CH2:29][C:30]([NH2:32])=[O:31])[C:10]=2[CH:9]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 867602083-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanamide

Product 1

HCID 248849123-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1h)-yl)propanamideYield 77%

Procedure

Demethylation of (118) prepared as described in example 231 with BBr3 using the procedure described in example 80 gave (119) as a yellow/orange powder (77%), mp 319–322° C. 1H NMR δ [(CD3)2SO] 11.06 (br s, 1H), 9.36 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.77 (s, 1H), 7.60–7.55 (m, 2H), 7.52–7.43 (m, 3H), 7.35 (br, 1H), 7.13 (dd, J=8.8, 2.4 Hz, 1H), 6.87 (br, 1H), 4.65 (t, J=6.7 Hz, 2H), 2.57 (t, J=6.7 Hz, 2H). FABMS found M+: 435.0833, 433.0828. C23H16ClN3O4 requires 435.0800, 433.0829.

Sources & evidence

ORD record
ord-0f624640443e434cbe5f5c9f361c5e94
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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