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

HRID 11020

반응식

HRID 11020 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.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1B(O)O>>[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1[C:8]1[C:7]2[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=2[C:5]2[C:4]3[CH:3]=[C:2]([OH:1])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1

참가 물질

3

반응물 2

HCID 5833222,6-Dimethylphenylboronic acidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

생성물 1

HCID 104509124-(2,6-dimethylphenyl)-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 2,6-dimethylbenzeneboronic acid according to the procedure described in example 8 gave 4-(2,6-dimethylphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (17) (I, Ar=2,6-dimethylphenyl) in a 62% yield; mp 230–238° C. (dec). 1H NMR δ [(CD3)2SO] 11.72 (s, 1H), 10.95 (s, 1H), 9.25 (s, 1H), 8.32 (d, J=2.3 Hz, 1H), 7.44 (d, J=8.7 Hz, 1H), 7.35 (s, 1H), 7.20 (t, J=7.5 Hz, 1H), 7.12 (d, J=7.5 Hz, 2H), 7.06 ((dd, J=8.7, 2.3 Hz, 1H), 1.93 (s, 6H). EIMS found M+: 356,1159, C22H16N2O3 requires 356,1161.

출처 및 근거

ORD 기록
ord-a3cbe4f73481439a9addb114abecb359
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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