3-Aminophenylboronic acid → 4-(3-aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11018

반응식

HRID 11018 반응식
[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.[NH2:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1>>[NH2:21][C:22]1[CH:27]=[C:26]([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:25]=[CH:24][CH:23]=1

참가 물질

3

반응물 2

HCID 922693-Aminophenylboronic acidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

생성물 1

HCID 99975354-(3-aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione수율 62%

실험 절차

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 3-aminobenzeneboronic acid according to the procedure described in example 8 gave 4-(3-aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (15) (I, Ar=3-aminophenyl) in a 62% yield; mp 279–284° C. 1H NMR δ [(CD3)2SO] 11.70 (s, 1H), 10.96 (s, 1H), 9.22 (s, 1H), 8.33 (d, J=2.4 Hz, 1H), 7.50 (s, 1H), 7.42 (d, J=8.7 Hz, 1H), 7.10–7.03 (m, 2H), 6.77–6.74 (m, 1H), 6.72–6.68 (m, 1H), 6.61 (dd, J=8.1, 2.3 Hz), 1H), 5.11 (br s, 2H). Found: C, 69.41; H, 4.12; N, 10.73. C20H13N3O3 requires C, 69.96; H, 3.82; N, 12.24.

출처 및 근거

ORD 기록
ord-b9a2e3ba2de040a58a6377e05c1dc1ef
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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