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2-(Bromomethyl)-5-(trifluoromethyl)furan → 6-fluoro-2'-oxo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile

HRID 1965658
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HRID 1965658 반응식
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][O:14]2)(=O)=O)=CC=1.BrCC1OC(C(F)(F)F)=CC=1.[F:29][C:30]1[C:35]([C:36]#[N:37])=[CH:34][C:33]2[C:38]3([CH2:48][O:49][C:32]=2[CH:31]=1)[C:46]1[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=1)[NH:40][C:39]3=[O:47].CC1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2ON=1>>[F:29][C:30]1[C:35]([C:36]#[N:37])=[CH:34][C:33]2[C:38]3([CH2:48][O:49][C:32]=2[CH:31]=1)[C:46]1[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=1)[N:40]([CH2:12][C@H:13]1[CH2:17][CH2:16][CH2:15][O:14]1)[C:39]3=[O:47]
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 593522716-Fluoro-2'-oxo-1,2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrileHCID 593524533-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3'-indol]-2'(1H)-one

생성물 1

HCID 67357777
6-fluoro-2'-oxo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile

실험 절차

Following the procedure as described in EXAMPLE 9 and making non-critical variations using (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, and 6-fluoro-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one, 6-fluoro-2′-oxo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile was obtained (34%): 1H NMR (300 MHz, CDCl3) δ 7.37-7.27 (m, 1H), 7.12-7.06 (m, 3H), 7.01-6.92 (m, 1H), 6.79-6.74 (m, 1H), 4.94 (ABq, 2H), 4.31-4.21 (m, 1H), 3.91-3.72 (m, 4H), 2.12-1.84 (m, 4H); MS (ES+) m/z 364.9 (M+1).

출처 및 근거

ORD 기록
ord-2aa020381b17484a903ebb7162a356f9
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415370B2

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