HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bis(pinacolato)diborane → 2-(5-(Dimethylamino)-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reactant | 2-Bromo-6-(5-(dimethylamino)-1-oxoisoindolin-2-yl)benzyl Acetate | HCID 66610297 | — |
| Reactant | 2-tert-Butyl-5-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-thieno[3,2-c]pyrrol-6(5H)-one | HCID 89824183 | — |
| Product | 2-(5-(Dimethylamino)-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Acetate | HCID 86699872 | 100% |
Reaction Steps
Using the same general procedure as described for the preparation of 102g reaction of 123d (2.65 g, 6.59 mmol) with bis(pinacolato)diboron (5.02 g, 19.8 mmol) gave a 100% yield (3.00 g) of 123e as a brown solid: mp 75-76° C.; 1H NMR (300 MHz, CDCl3) δ 7.85 (dd, 1H, J=4.2, 1.8 Hz), 7.76 (d, 1H, J=8.7 Hz), 7.45 (m, 2H), 6.80 (dd, 1H, J=8.7, 2.1 Hz), 6.69 (s, 1H), 5.13 (s, 2H), 4.69 (s, 2H), 3.08 (s, 6H), 1.93 (s, 3H), 1.34 (s, 12H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09249123B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-314f124837b74401b5ffd643a401f4fa |
| Source note | uspto-grants-2016_02 |