3-Bromophenol → 1-hydroxy-1-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-3-(4-methoxybenzyl)-1,3-dihydro-2H-pyrrolo[3,2-f]quinolin-2-one

HRID 2385071Notes

Reaction equation

HRID 2385071 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.BrC1C=C(O)C=CC=1.[CH3:19][O:20][C:21]1[CH:42]=[CH:41][C:24]([CH2:25][N:26]2[C:38]3[C:29](=[C:30]4[C:35](=[CH:36][CH:37]=3)[N:34]=[CH:33][CH:32]=[CH:31]4)[C:28](=[O:39])[C:27]2=[O:40])=[CH:23][CH:22]=1.FC(F)(F)C1OC(CN2C3C(=CC=CC=3)C(=O)C2=O)=CC=1>>[OH:39][C:28]1([C:8]2[C:7]([OH:10])=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)[C:29]2=[C:30]3[C:35](=[CH:36][CH:37]=[C:38]2[N:26]([CH2:25][C:24]2[CH:41]=[CH:42][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[C:27]1=[O:40])[N:34]=[CH:33][CH:32]=[CH:31]3

Participants

5

Reactant 4

HCID 115633-BromophenolHCID 122365402,3-Dihydro-1-benzofuran-6-olHCID 673564881-((5-(Trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dioneHCID 685988063-(4-methoxybenzyl)-1H-pyrrolo[3,2-f]quinoline-1,2(3H)-dione

Product 1

HCID 673572741-hydroxy-1-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-3-(4-methoxybenzyl)-1,3-dihydro-2H-pyrrolo[3,2-f]quinolin-2-one

Procedure

Following the procedure as described in PREPARATION 2A and making non-critical variations using 2,3-dihydrobenzofuran-6-ol to replace 3-bromophenol, and 3-(4-methoxybenzyl)-1H-pyrrolo[3,2-f]quinoline-1,2(3H)-dione to replace 1-((5-(trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione, 1-hydroxy-1-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-3-(4-methoxybenzyl)-1,3-dihydro-2H-pyrrolo[3,2-f]quinolin-2-one was obtained (58%) as a colorless solid: MS (ES+) m/z 455.0 (M+1).

Sources & evidence

ORD record
ord-08d80bad31694e4687c68840d29203aa
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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