Phenylboronic Acid → tert-butyl 1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethylcarbamate

HRID 634412Notes

Reaction equation

HRID 634412 reaction equation
OC(C1[O:5][C:6](=[O:20])[C:7]2[C:12](C=1C1C=CC=CC=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)C.Br[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)C(=O)O[C:23]=1[CH:33]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH3:34].C1(B(O)O)C=CC=CC=1>>[O:20]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:22]([C:31]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[C:23]([CH:33]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH3:34])[O:5]1

Participants

4

Reactant 3

HCID 66827Phenylboronic AcidHCID 118131111tert-butyl 1-(4-bromo-1-oxo-1H-isochromen-3-yl)ethylcarbamate2×HCID 1181311643-(1-Hydroxyethyl)-4-phenyl-1H-isochromen-1-one

Product 1

HCID 118131293tert-butyl 1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethylcarbamateYield 22.6%

Procedure

The title compound was made in a way similar to that of intermediate B1 from tert-butyl 1-(4-bromo-1-oxo-1H-isochromen-3-yl)ethylcarbamate (Intermediate A3, 500 mg, 1.358 mmol), phenylboronic acid (215 mg, 1.765 mmol), to give the title compound (112 mg, 22.6%) as a yellowish oil.

Sources & evidence

ORD record
ord-8ba473e6d66d49c5be410ed3e1eeebc0
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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