2-(5-tert-Butyl-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Acetate → HCID 178480060, compound

HRID 1772107Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[NH:15][N:14]=[C:13]([CH:16]3[CH2:18][CH2:17]3)[CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.C([O:22][CH2:23][C:24]1[C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][CH:27]=[CH:26][C:25]=1[N:39]1[CH2:47][C:46]2[C:41](=[CH:42][CH:43]=[C:44]([C:48]([CH3:51])([CH3:50])[CH3:49])[CH:45]=2)[C:40]1=[O:52])(=O)C>>[C:48]([C:44]1[CH:45]=[C:46]2[C:41](=[CH:42][CH:43]=1)[C:40](=[O:52])[N:39]([C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([C:2]3[CH:3]=[C:4]([NH:10][C:11]4[NH:15][N:14]=[C:13]([CH:16]5[CH2:18][CH2:17]5)[CH:12]=4)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=3)[C:24]=1[CH2:23][OH:22])[CH2:47]2)([CH3:51])([CH3:49])[CH3:50]

Participants

Reactant 2

HCID 866979362-(5-tert-Butyl-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Acetate

HCID 178479983HCID 178479983, compound

Product 1

HCID 178480060HCID 178480060, compoundYield 33%

Procedure

Using the same general procedure as Example 105, reaction of 110a (260 mg, 0.841 mmol) and 103f (429 mg, 0.926 mmol) afforded a 33% yield (144 mg) of 110 as an off-white solid: mp 178-180° C.; 1H NMR (500 MHz, DMSO-d6) δ 11.76 (d, 1H, J=2.0 Hz), 7.98 (d, 1H, J=2.0 Hz), 7.92 (s, 1H), 7.71 (m, 2H), 7.61 (dd, 1H, J=7.9, 1.6 Hz), 7.48 (m, 1H), 7.42 (dd, 1H, J=7.6, 1.1 Hz), 7.35 (dd, 1H, J=7.6, 1.1 Hz), 7.23 (d, 1H, J=2.1 Hz), 5.79 (d, 1H, J=2.2 Hz), 4.93 (s, 2H), 4.90 (t, 1H, J=4.9 Hz), 4.35 (d, 2H, J=4.6 Hz), 3.57 (s, 3H), 1.81 (m, 1H), 1.37 (s, 9H), 0.89 (m, 2H), 0.64 (m, 2H); MS (ESI+) m/z 524.2 (M+H).

Sources & evidence

ORD record: ord-d300d669ee4c4fc3ad6ab0b090e3de0d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249123B2

Reaction notes

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