2-Bromo-1-fluoro-4-nitrobenzene → 4-Difluoromethoxy-3-(4-nitro-2-bromophenoxy)benzaldehyde

HRID 1788086

反応式

HRID 1788086 の反応式
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[OH:12].[Br:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1F.[F-].[K+]>>[F:1][CH:2]([F:13])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[O:12][C:16]1[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=1[Br:14]

参加物

4

反応物 3

HCID 696992-Bromo-1-fluoro-4-nitrobenzeneHCID 522689Potassium FluorideHCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehyde

生成物 1

HCID 247582824-Difluoromethoxy-3-(4-nitro-2-bromophenoxy)benzaldehyde

実験手順

In other embodiments, the present invention provides methods of preparing N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfonamide-dibenzo[b,d]furan-1-carboxamide, as shown in FIG. 1. For example, 4-difluoromethoxy-3-hydroxybenzaldehyde may be reacted with 2-bromo-1-fluoro-4-nitrobenzene in a first solvent comprising potassium fluoride to produce 4-difluoromethoxy-3-(4-nitro-2-bromophenoxy)benzaldehyde (scheme I). In a second step, the 4-difluoromethoxy-3-(4-nitro-2-bromophenoxy)benzaldehyde may be cyclized in a second solvent comprising a catalyst to produce 4-difluoromethoxy-8-nitro-1-formyl dibenzofuran (scheme II). In a third step, the 4-difluoromethoxy-8-nitro-1-formyl dibenzofuran may be oxidized in a third solvent comprising an oxidizing agent to produce 4-difluoromethoxy-8-nitrobenzo[b,d]furan-1-carboxylic acid (scheme III). In a fourth step, 4-difluoromethoxy-8-nitrobenzo[b,d]furan-1-carboxylic acid may be reacted in a fourth solvent comprising an inorganic acid halide, 4-amino-3,5-dichloropyridine and a first base to produce N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (scheme IV). In a fifth step, N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide may be reduced in the presence of a reducing agent to produce N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide. Suitable reducing agents include, but are not limited to, zinc, indium, iron, tin, Raney-nickel and sodium borohydride. In a sixth step, the N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide may be reacted in a fifth solvent comprising methanesulfonyl chloride and a second base to produce N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-(methanesulfonamide)dibenzo[b,d]furan-1-carboxamide.

後処理

  1. customIn other embodiments, the present invention provides

出典と根拠

ORDレコード
ord-715f96d68ecf4b60b50b33ade046d8dd
出典データセット
uspto-grants-2009_03
特許番号
US07511150B2

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