3-Bromophenol → 6-(diphenylmethyl)-8-hydroxy-8-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-2,3,6,8-tetrahydro-7H-[1,4]dioxino[2,3-f]indol-7-one

HRID 1407487Notes

Reaction equation

HRID 1407487 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.[C:19]1([CH:25]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:26]2[C:34]3[CH:33]=[C:32]4[O:35][CH2:36][CH2:37][O:38][C:31]4=[CH:30][C:29]=3[C:28](=[O:39])[C:27]2=[O:40])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.FC(F)(F)C1OC(CN2C3C(=CC=CC=3)C(=O)C2=O)=CC=1>>[C:41]1([CH:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:26]2[C:34]3[CH:33]=[C:32]4[O:35][CH2:36][CH2:37][O:38][C:31]4=[CH:30][C:29]=3[C:28]([OH:39])([C:8]3[C:7]([OH:10])=[CH:6][C:5]4[O:1][CH2:2][CH2:3][C:4]=4[CH:9]=3)[C:27]2=[O:40])[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

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 673802436-(diphenylmethyl)-2,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dione

Product 1

HCID 686012706-(diphenylmethyl)-8-hydroxy-8-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-2,3,6,8-tetrahydro-7H-[1,4]dioxino[2,3-f]indol-7-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 6-(diphenylmethyl)-2,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dione to replace 1-((5-(trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione, 6-(diphenylmethyl)-8-hydroxy-8-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-2,3,6,8-tetrahydro-7H-[1,4]dioxino[2,3-f]indol-7-one was obtained (94%) as a colorless solid: MS (ES−) m/z 506.1 (M−1).

Sources & evidence

ORD record
ord-cb659b9d9eef4dfa866136ada431755e
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

Loading…