Thiophene-3-boronic acid → 9-hydroxy-4-(3-thienyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11017

반응식

HRID 11017 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.[S:21]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22]1>>[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:23]4[CH:24]=[CH:25][S:21][CH:22]=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

참가 물질

3

반응물 2

HCID 581760Thiophene-3-boronic acidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

생성물 1

HCID 118434289-hydroxy-4-(3-thienyl)pyrrolo[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 3-thienylboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-(3-thienyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (12) (I, Ar=3-thienyl) in a 74% yield; mp 247° C. (dec). 1H NMR δ [(CD3)2SO] 11.73 (br s, 1H), 11.05 (br s, 1H), 9.24 (s, 1H), 9.15 (s, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.92 (dd, J=5.0, 2.7 Hz, 1H), 7.70 (s, 1H), 7.61 (dd, J=5.0, 2.7 Hz, 1H), 7.51 (dd, J=5.0, 0.9 Hz, 1H), 7.42 (d, J=8.7 Hz, 1H), 7.06 (dd, J=8.7, 2.4 Hz, 1H). Found: C, 61.05; H, 2.96; N, 7.60. C18H10N2SO3,H2O requires C, 61.36; H, 3.43; N, 7.95.

출처 및 근거

ORD 기록
ord-3e8055b9779548408caffc318cb31728
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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