Methylamine → HCID 57823927, compound

HRID 656808Notes

Reaction equation

HRID 656808 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[C:11]([CH:17]3[CH2:19][CH2:18]3)[C:12]([C:14](=[O:16])[CH3:15])=[CH:13][C:8]=2[O:7][C:6]=1[C:20]1[CH:25]=[CH:24][C:23](OC2C=CC=CC=2)=[CH:22][CH:21]=1)=[O:4].[F:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1.CN.[CH3:43][Mg]Br>>[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[C:11]([CH:17]3[CH2:18][CH2:19]3)[C:12]([C:14]([OH:16])([CH3:15])[CH3:43])=[CH:13][C:8]=2[O:7][C:6]=1[C:20]1[CH:21]=[CH:22][C:23]([O:40][C:37]2[CH:38]=[CH:39][C:34]([F:33])=[CH:35][CH:36]=2)=[CH:24][CH:25]=1)=[O:4]

Participants

5

Reactant 4

HCID 6329MethylamineHCID 97324-FluorophenolHCID 57823936HCID 57823936, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57823927HCID 57823927, compound

Procedure

I-86 is prepared analogously except the starting material was 6-acetyl-5-cyclopropyl-2-(4-phenoxy-phenyl)-benzofuran-3-carboxylic acid methylamide. I-103 and I-104 can be prepared from A-2c by introduction of the p-fluorophenyl by Suzuki coupling with p-fluoro-phenol (see step 5 of example 3), Freidel-Crafts acylation, hydrolysis of the ethyl ester and coupling with methylamine and addition of methyl magnesium bromide as carried described in the current example.

Workup

  1. customI-86 is prepared analogously except the starting material

Sources & evidence

ORD record
ord-3a3e143136074aae877bc849e7ddb668
Source dataset
uspto-grants-2011_12
Patent number
US08071797B2

Reaction notes

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