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

HRID 425028Notes

Reaction equation

HRID 425028 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].Br[C:37]1C=CC(I)=C(C)C=1>>[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][C:22]=1[CH3:37])[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 27246015-Bromo-2-iodotolueneHCID 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 59243602Cyclopentyl(2S,4E)-2-[(tert-butoxycarbonyl)amino]-5-[2-methyl-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-2-methyl-iodobenzene at Stage 2 of Scheme 4. m/z 500 [M+H]+.

Sources & evidence

ORD record
ord-77289b17995f4000bbbf00ff38696c8d
Source dataset
uspto-grants-2012_01
Patent number
US08106091B2

Reaction notes

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