Boron tribromide → HCID 21980394, compound

HRID 11048Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24]C)[C:14]3[C:26](=[O:30])[NH:27][C:28](=[O:29])[C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([O:31]C)[CH:8]=[CH:7][C:6]1=2.B(Br)(Br)Br>>[OH:31][C:9]1[CH:8]=[CH:7][C:6]2[N:5]([CH2:4][CH2:3][CH2:2][OH:1])[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[OH:24])[C:14]4[C:26](=[O:30])[NH:27][C:28](=[O:29])[C:13]=4[C:12]=3[C:11]=2[CH:10]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 867601936-(3-Hydroxypropyl)-9-methoxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 21980394HCID 21980394, compoundYield 82%

Procedure

The reaction of 6-(3-Hydroxypropyl)-9-methoxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-methoxyphenyl, R10═CH2CH2CH2OH) (100) prepared as described in example 53 with BBr3 using the procedure described in example 80 gave 9-Hydroxy-4-(2-hydroxyphenyl)-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-hydroxyphenyl, R10═CH2CH2CH2OH) (101) in an 82% yield as an orange powder, mp 306–309° C. 1H NMR δ [(CD3)2SO] 10.90 (br, 1H), 9.40 (br, 1H), 8.38 (d, J=2.4 Hz, 1H), 7.67 (s, 1H), 7.56 (d, J=8.8 Hz, 1H), 7.30–7.23 (m, 2H), 7.13 (dd, J=8.8, 2.4 Hz, 1H), 6.94–6.88 (m, 2H), 4.78 (br, 2H), 4.47 (t, J=6.8 Hz, 2H), 3.41 (t, J=6.0 Hz, 2H), 1.91 (m, 2H). Found: C, 66.85; H, 4.61; N, 6.63. C23H18N2O5.1/2H2O requires C, 67.14; H, 4.65; N, 6.80.

Sources & evidence

ORD record: ord-8c86a68d22c44256bfbf666ba786b6a7
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094798B1

Reaction notes

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