Boron tribromide → HCID 9981225, compound

HRID 11051Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([O:28]C)[CH:16]=[CH:15][C:14]=3[N:13]([CH2:30][CH2:31][CH2:32][OH:33])[C:12]=2[CH:11]=1.B(Br)(Br)Br>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([OH:28])[CH:16]=[CH:15][C:14]=3[N:13]([CH2:30][CH2:31][CH2:32][OH:33])[C:12]=2[CH:11]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 867601964-(2-Chloro-6-methoxyphenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 9981225HCID 9981225, compoundYield 64%

Procedure

The reaction of 4-(2-Chloro-6-methoxyphenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OH) (105) prepared as described in example 58 with BBr3 using the procedure described in example 80 and with a reaction time of 90 minutes gave 4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OH) (106) in a 64% yield as an orange powder, mp 270–273° C. 1H NMR δ [(CD3)2SO] 11.01 (br s, 1H), 9.35 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.70 (s, 1H), 7.58 (d, J=8.7 Hz, 1H), 7.44 (dd, J=8.3, 8.3 Hz, 1H), 7.20–7.11 (m, 3H), 4.61 (br t, 1H), 4.47 (t, J=6.9 Hz, 2H), 3.68 (s, 3H), 3.42 (m, 2H), 1.88 (m, 2H). Found: C, 64.16; H, 4.55; N, 6.01. C24H19ClN2O5 requires C, 63.93; H, 4.25; N, 6.21.

Workup

customdescribed in example 80 and with a reaction time of 90 minutes

Sources & evidence

ORD record: ord-60079b1f24ca45af8dc55a802fe52b64
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094798B1

Reaction notes

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