1-Bromo-2-chloro-4-iodobenzene → Cyclopentyl(2S,4E)-2-[(tert-butoxycarbonyl)amino]-5-[3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pent-4-enoate

HRID 425027Notes

Reaction equation

HRID 425027 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([B:27]2[O:31][C:30]([CH3:33])([CH3:32])[C:29]([CH3:35])([CH3:34])[O:28]2)=[CH:23][CH:22]=1)[C:10]([O:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].BrC1C=CC(I)=CC=1[Cl:44]>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([B:27]2[O:31][C:30]([CH3:33])([CH3:32])[C:29]([CH3:35])([CH3:34])[O:28]2)=[C:23]([Cl:44])[CH:22]=1)[C:10]([O:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 27568861-Bromo-2-chloro-4-iodobenzeneHCID 59243623cyclopentyl(2S,4E)-2-[(tert-butoxycarbonyl)amino]-5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pent-4-enoate

Product 1

HCID 59243614Cyclopentyl(2S,4E)-2-[(tert-butoxycarbonyl)amino]-5-[3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pent-4-enoate

Procedure

Synthesised by analogous methods to Intermediate 5a, using 4-bromo-3-chloro-iodobenzene at Stage 2 of Scheme 4. m/z 520 [M+H]+.

Sources & evidence

ORD record
ord-d9d211573f194dd7844e1b7414845a50
Source dataset
uspto-grants-2012_01
Patent number
US08106091B2

Reaction notes

Loading…