(2-Ethoxyphenyl)boronic acid → 4-(2-ethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11029

반응식

HRID 11029 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.[CH2:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O)[CH3:22]>>[CH2:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=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)[CH3:22]

참가 물질

3

반응물 2

HCID 2734902(2-Ethoxyphenyl)boronic acidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

생성물 1

HCID 118430014-(2-ethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione수율 74%

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-ethoxybenzeneboronic acid according to the procedure described in example 8 gave 4-(2-ethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (504) (I; Ar=2-ethoxyphenyl) in a 74% yield; mp (THF/CH2Cl2/hexane) 190–193° C. (dec). 1H NMR [(CD3)2SO] δ 11.71 (br s, 1H), 10.91 (br s, 1H), 9.23 (s, 1H), 8.31 (d, J=2.4 Hz, 1H), 7.51 (s, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.38 (td, J=7.8, 1.7 Hz, 1H), 7.33 (dd, J=7.5, 1.7 Hz, 1H), 7.07 (br d, J=6.7 Hz, 1H), 7.05 (dd, J=8.7, 2.3 Hz, 1H), 7.02 (dd, J=7.3, 6.6 Hz, 1H), 3.97 (q, J=6.7 Hz, 2H), 1.11 (t, J=6.9 Hz, 3H). Found: C, 70.63; H, 4.74; N, 6.88. C22H16N2O4.1/4 THF requires C, 70.76; H, 4.65; N, 7.18.

출처 및 근거

ORD 기록
ord-20d287d6f64d4e9ea73641b7925232f5
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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