N-Methylallylamine → Allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine

HRID 342210

Reaction equation

BrC1C=CC(C2C3C=CC(O)=CC=3OC=2)=CC=1.BrC/C=C/CBr.Br[CH2:25]/[CH:26]=[CH:27]/[CH2:28][O:29][C:30]1[CH:45]=[CH:44][C:33]2[C:34]([C:37]3[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=3)=[CH:35][O:36][C:32]=2[CH:31]=1.[CH2:46]([NH:49][CH3:50])[CH:47]=[CH2:48]>>[CH2:46]([N:49]([CH2:25]/[CH:26]=[CH:27]/[CH2:28][O:29][C:30]1[CH:45]=[CH:44][C:33]2[C:34]([C:37]3[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=3)=[CH:35][O:36][C:32]=2[CH:31]=1)[CH3:50])[CH:47]=[CH2:48]

Participants

Reactant 4

HCID 69391N-Methylallylamine

HCID 641245trans-1,4-Dibromo-2-butene

HCID 545619733-(4-Bromo-phenyl)benzofuran-6-ol

HCID 67596496(E)-6-(4-bromo-but-2-enyloxy)-3-(4-bromo-phenyl)-benzofuran

Product 1

HCID 447559Allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine

Procedure

Analogously to Example 1, from 3-(4-bromo-phenyl)benzofuran-6-ol and (E)-1,4-dibromo-2-butene via (E)-6-(4-bromo-but-2-enyloxy)-3-(4-bromo-phenyl)-benzofuran and by reaction with N-allyl-methyl-amine there is obtained (E)-allyl-[4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl]-methyl-amine which is converted into the fumarate, MS: m/e 412 (M+H+, 1 Br).

Sources & evidence

ORD record: ord-c8cae310a44d419a845e947d7d058436
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856503

Linked notes

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