(2,3-Dihydro-1-benzofuran-5-yl)boronic acid → HCID 66799948, compound

HRID 589797Notes

Reaction equation

HRID 589797 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].[O:22]1[C:26]2[CH:27]=[CH:28][C:29](B(O)O)=[CH:30][C:25]=2[CH2:24][CH2:23]1>>[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:29]1[CH:28]=[CH:27][C:26]2[O:22][CH2:23][CH2:24][C:25]=2[CH:30]=1

Participants

3

Reactant 2

HCID 2773380(2,3-Dihydro-1-benzofuran-5-yl)boronic acidHCID 66799929HCID 66799929, compound2×

Product 1

HCID 66799948HCID 66799948, compoundYield 46%

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 2,3-dihydrobenzofuran-5-boronic acid (9 mg, 0.055 mmol) according to the General Procedure 12, described in Example 135. The title compound was obtained in 46% yield (10.6 mg). 1H NMR (500 MHz, MeOH-d4) δ ppm 3.23 (t, J=8.70 Hz, 2 H) 4.58 (t, J=8.70 Hz, 2 H) 6.76 (d, J=8.24 Hz, 1 H) 6.90 (t, J=7.95 Hz, 1 H) 7.14-7.17 (ddt, J=8.24, 1.97, 0.71 Hz, 1 H) 7.25 (dt, J=1.97, 1.30 Hz, 1 H) 7.31 (s, 1 H) 7.66 (dd, J=7.95, 1.65 Hz, 1 H) 7.74 (dd, J=7.95, 1.65 Hz, 1 H). MS (ESI+) m/z 452 [M+H]+.

Sources & evidence

ORD record
ord-4865ecb9773944c39fa788f8d78fde2f
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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