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2-(Bromomethyl)pyridine hydrobromide → 6-Fluoro-2'-oxo-1'-(pyridin-2-ylmethyl)-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile

HRID 1407791
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HRID 1407791 반응식
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.BrCC1OC(C(F)(F)F)=CC=1.[F:21][C:22]1[C:27]([C:28]#[N:29])=[CH:26][C:25]2[C:30]3([CH2:40][O:41][C:24]=2[CH:23]=1)[C:38]1[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=1)[NH:32][C:31]3=[O:39].CC1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2ON=1>>[F:21][C:22]1[C:27]([C:28]#[N:29])=[CH:26][C:25]2[C:30]3([CH2:40][O:41][C:24]=2[CH:23]=1)[C:38]1[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=1)[N:32]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[C:31]3=[O:39]
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참가 물질

5

반응물 4

HCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 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 593524116-Fluoro-2'-oxo-1'-(pyridin-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 2-(bromomethyl)pyridine hydrobromide 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′-(pyridin-2-ylmethyl)-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile was obtained (55%): mp 108-109° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.71-7.66 (m, 1H), 7.29-7.20 (m, 3H), 7.15-7.03 (m, 3H), 6.93-6.90 (m, 1H), 6.79-6.76 (m, 1H), 5.26-4.85 (m, 4H); MS (ES+) m/z 371.9 (M+1).

출처 및 근거

ORD 기록
ord-f248c3c51c0743d9b46116df56a09aa9
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08916580B2

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