4-(Dimethylamino)phenylboronic acid → HCID 11359174, compound

HRID 969982Notes

Reaction equation

Br[C:2]1[CH:16]=[CH:15][C:5]([O:6][C@@H:7]2[CH:12]3[CH2:13][CH2:14][N:9]([CH2:10][CH2:11]3)[CH2:8]2)=[CH:4][CH:3]=1.[CH3:17][N:18]([CH3:28])[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>>[N:9]12[CH2:14][CH2:13][CH:12]([CH2:11][CH2:10]1)[C@@H:7]([O:6][C:5]1[CH:15]=[CH:16][C:2]([C:22]3[CH:23]=[CH:24][C:19]([N:18]([CH3:28])[CH3:17])=[CH:20][CH:21]=3)=[CH:3][CH:4]=1)[CH2:8]2

Participants

Reactant 2

HCID 27343444-(Dimethylamino)phenylboronic acid

HCID 67070131HCID 67070131, compound

Product 1

HCID 11359174HCID 11359174, compound

Procedure

The product of Example 9B (282 mg, 1 mmol) was treated with N,N-dimethyl-4-amino-phenyl boronic acid (230 mg, 1.4 mmol) according to the procedure of Example 1B. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.2) as a solid (118 mg, yield, 37%). 1H NMR (MeOH-d4, 300 MHz) δ 1.41-1.56 (m, 1H), 1.61-1.88 (m, 2H), 1.98-2.12 (m, 1H), 2.14-2.22 (m, 1H), 2.72-3.01 (m, 11H), 3.22-3.34 (m, 1H), 4.48-4.57 (m, 1H), 6.83 (dt, J=8.8, 3.0 Hz, 2H), 6.92 (dt, J=8.8, 2.1 Hz, 2H), 7.39-7.49 (m, 4H) ppm. MS (DCl/NH3) m/z 323 (M+H)+.

Workup

customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.2) as a solid (118 mg, yield, 37%)

Sources & evidence

ORD record: ord-116108aed94746479692e219e240d9f0
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07309699B2

Reaction notes

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