Bis(pinacolato)diborane → 2-(5-(Dimethylamino)-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Acetate

HRID 1772151Notes

Reaction equation

HRID 1772151 reaction equation
C(C1SC2C(=O)N(C3C=CC=C([B:20]4[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]4)C=3C)CC=2C=1)(C)(C)C.[C:30]([O:33][CH2:34][C:35]1[C:40]([N:41]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[C:46]([N:50]([CH3:52])[CH3:51])[CH:47]=3)[C:42]2=[O:53])=[CH:39][CH:38]=[CH:37][C:36]=1Br)(=[O:32])[CH3:31].B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1>>[C:30]([O:33][CH2:34][C:35]1[C:36]([B:20]2[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]2)=[CH:37][CH:38]=[CH:39][C:40]=1[N:41]1[CH2:49][C:48]2[C:43](=[CH:44][CH:45]=[C:46]([N:50]([CH3:52])[CH3:51])[CH:47]=2)[C:42]1=[O:53])(=[O:32])[CH3:31]

Participants

4

Reactant 3

HCID 2733548Bis(pinacolato)diboraneHCID 666102972-Bromo-6-(5-(dimethylamino)-1-oxoisoindolin-2-yl)benzyl AcetateHCID 898241832-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

Product 1

HCID 866998722-(5-(Dimethylamino)-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl AcetateYield 100%

Procedure

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).

Sources & evidence

ORD record
ord-314f124837b74401b5ffd643a401f4fa
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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