4-Bromo-3-(6-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(hydroxymethyl)indolin-2-one → 4'-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1H)-one

HRID 425610

반응식

HRID 425610 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:14]1[C:22]([OH:23])=[CH:21][C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=1)([CH2:12]O)[C:5](=[O:11])[NH:6]2.ClC1C=CC(Cl)=C2C=1C(C1C(O)=CC3OCOC=3C=1)(CO)C(=O)N2CCCCC>>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([C:14]3=[CH:15][C:16]4[O:20][CH2:19][O:18][C:17]=4[CH:21]=[C:22]3[O:23][CH2:12]1)[C:5](=[O:11])[NH:6]2

참가 물질

3

반응물 2

HCID 588724444-Bromo-3-(6-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(hydroxymethyl)indolin-2-oneHCID 588724744,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one

생성물 1

HCID 592633724'-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1H)-one수율 71%

실험 절차

Following the procedure as described in EXAMPLE 1.22, and making non-critical variations using 4-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one to replace 4,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one, the title compound was obtained in 71% yield as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ 10.79 (s, 1H), 7.19-7.08 (m, 2H), 6.90 (dd, 1H), 6.58 (s, 1H), 6.25 (s, 1H), 5.90 (d, 2H), 4.74 (ABq, 2H); 13C NMR (75 MHz, DMSO-d6) δ 178.5, 157.0, 148.8, 144.5, 141.9, 131.2, 130.6, 126.1, 119.2, 117.5, 109.8, 103.3, 101.8, 93.3, 77.6, 59.7; MS (ES−) m/z 360.4 (M−1), 358.4 (M−1).

출처 및 근거

ORD 기록
ord-587364d070fb43abb091986ba18690c2
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106087B2

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