4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → 4-(4-aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11019

反応式

HRID 11019 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.CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)O1>>[NH2:35][C:32]1[CH:33]=[CH:34][C:29]([C:8]2[C:7]3[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=3[C:5]3[C:4]4[CH:3]=[C:2]([OH:1])[CH:14]=[CH:13][C:12]=4[NH:11][C:10]=3[CH:9]=2)=[CH:30][CH:31]=1

参加物

3

反応物 2

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

生成物 1

HCID 118432894-(4-aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione収率 57%

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-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine according to the procedure described in example 8 gave 4-(4-Aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (16) (I, Ar=4-aminophenyl) in a 57% yield; mp 256–258° C. 1H NMR δ [(CD3)2SO] 11.60 (s, 1H), 10.92 (s, 1H), 9.19 (s, 1H), 8.31 (d, J=2.3 Hz, 1H), 7.48 (s, 1H), 7.39 (d, J=8.6 Hz, 1H), 7.30 (d, J=8.4 Hz, 2H), 7.02 (dd, J=8.6, 2.3 Hz, 1H), 6.62 (d, J=8.4 Hz, 2H), 5.29 (br s, 2H). Found: C, 68.09; H, 4.34; N, 11.03. C20H13N3O3.1/2H2O requires C, 68.17; H, 4.00; N, 11.92.

出典と根拠

ORDレコード
ord-03f61ac48ef24891b73944c38c052aba
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

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