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

HRID 11033

反応式

HRID 11033 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:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=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:26]4[CH:27]=[CH:28][C:23]([CH:21]=[O:22])=[CH:24][CH:25]=4)[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 5910734-Formylphenylboronic AcidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

生成物 1

HCID 219809164-(9-Hydroxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)benzaldehyde収率 52%

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 4-formylbenzeneboronic acid according to the procedure described in example 8 gave 4-(9-hydroxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)benzaldehyde (509) (I; Ar=4-formylphenyl) in a 52% yield; mp (THF/CH2Cl2/pentane) 276–280° C. 1H NMR [(CD3)2SO] δ 11.84 (br s, 1H), 11.07 (br s, 1H), 10.11 (s, 1H), 9.28 (br s, 1H), 8.34 (d, J=2.3 Hz, 1H), 8.00 (d, J=8.2 Hz, 2H), 7.85 (d, J=8.1 Hz, 2H), 7.65 (s, 1H), 7.46 (d, J=8.7 Hz, 1H), 7.08 (dd, J=8.7, 2.4 Hz, 1H). Found: C, 68.43; H, 4.16; N, 7.26. C21H12N2O4.3/4H2O requires C, 68.20; H, 3.68; N, 7.57. FABMS found [M+H]+: 357.0841. C21H13N2O4 requires 357.0875.

出典と根拠

ORDレコード
ord-34dbcb15aab6471fb2c36dc4fe0fdbfe
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

関連ノート

読み込み中…