2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66800076, compound

HRID 589798Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:13]([OH:21])=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])(=[O:10])=[O:9])[S:5][C:6]=1[Cl:7].CC1(C)C(C)(C)OB([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[OH:36])O1>>[Cl:7][C:6]1[S:5][C:4]([S:8]([NH:11][C:12]2[C:13]([OH:21])=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])(=[O:10])=[O:9])=[CH:3][C:2]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[OH:36]

Participants

Reactant 2

HCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

HCID 66799929HCID 66799929, compound2×

Product 1

HCID 66800076HCID 66800076, compoundYield 24%

Procedure

The product was prepared from 3-{[(4-bromo-5-chlorothiophen-2-yl)sulfonyl]amino}-2-hydroxybenzoic acid (Intermediate 22) (20.6 mg, 0.050 mmol) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (11 μl, 0.055 mmol) according to the General Procedure 12, described in Example 135. The title compound was obtained in 24% yield (5.3 mg). 1H NMR (500 MHz, MeOH-d4) δ ppm 6.85 (ddd, J=7.60, 7.32, 1.15 Hz, 1 H) 6.87 (ddd, J=8.21, 1.15, 0.45 Hz, 1 H) 6.88 (t, J=7.95 Hz, 1 H) 7.15 (ddd, J=7.60, 1.71, 0.45 Hz, 1 H) 7.20 (ddd, J=8.21, 7.32, 1.71 Hz, 1 H) 7.39 (s, 1 H) 7.65 (dd, J=7.95, 1.65 Hz, 1 H) 7.71 (dd, J=7.95, 1.65 Hz, 1 H). MS (ESI+) m/z 426 [M+H]+.

Sources & evidence

ORD record: ord-e93fb5f5a55a4427bdb40ecd0d80af74
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

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