3-Formylphenylboronic acid → 3-(9-Hydroxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)benzaldehyde

HRID 11031

反応式

HRID 11031 の反応式
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8](I)[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1.[CH:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22]>>[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:27]4[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=4)[CH:21]=[O:22])[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1

参加物

3

反応物 2

HCID 27343563-Formylphenylboronic acidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

生成物 1

HCID 219807333-(9-Hydroxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)benzaldehyde収率 69%

実験手順

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 3-formylbenzeneboronic acid according to the procedure described in example 8 gave 3-(9-Hydroxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)benzaldehyde (507) (I; Ar=3-formylphenyl) in a 69% yield; mp (THF/CH2Cl2/pentane) 280–286° C. (dec). 1H NMR [(CD3)2SO] δ 11.82 (br s, 1H), 11.07 (br s, 1H), 10.11 (s, 1H), 9.27 (br s, 1H), 8.35 (d, J=2.4 Hz, 1H), 8.14 (t, J=1.4 Hz, 1H), 7.97 (m, 2H), 7.70 (t, J=7.7 Hz, 2H), 7.65 (s, 1H), 7.46 (d, J=8.7 Hz, 1H), 7.08 (dd, J=8.7, 2.5 Hz, 1H). FABMS found [M+H]+: 357.0857. C21H13N2O4 requires 357.0875.

出典と根拠

ORDレコード
ord-6364c659f35d44cfb4db8b5ef35cce51
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

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