1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → [1-((Rac)-5-bromo-7-fluoro-indan-1-ylcarbamoyl)-cyclopropyl]-carbamic acid tert-butyl ester
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[CH:7]([NH2:12])[CH2:6][CH2:5]2.[C:13]([O:17][C:18]([NH:20][C:21]1([C:24](O)=[O:25])[CH2:23][CH2:22]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18](=[O:19])[NH:20][C:21]1([C:24](=[O:25])[NH:12][CH:7]2[C:8]3[C:4](=[CH:3][C:2]([Br:1])=[CH:10][C:9]=3[F:11])[CH2:5][CH2:6]2)[CH2:22][CH2:23]1)([CH3:16])([CH3:14])[CH3:15]Participants
3
Procedure
In analogy to the procedures described for the preparation of intermediate A-1 [B] and for the preparation of example 12, (rac)-5-bromo-7-fluoro-indan-1-ylamine (intermediate A-7 [C]) has been coupled with 1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid to give [1-((rac)-5-bromo-7-fluoro-indan-1-ylcarbamoyl)-cyclopropyl]-carbamic acid tert-butyl ester, which was then reacted with 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) and (1,1′-bis-diphenylphosphino)-ferrocene)palladium-(II)dichloride (1:1 complex with CH2Cl2) and subsequently with 3-(2-bromo-4-chloro-6-fluoro-phenyl)-5-methyl-[1,2,4]oxadiazole (intermediate B-2) to give the title compound as light brown solid. MS: 545.2 (MH+, 1Cl).
Sources & evidence
- ORD record
- ord-fa98511c2e374811b106c773b2a8cad8
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592426B2
Reaction notes
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