3-Aminophenylboronic acid → HCID 11437893, compound

HRID 969986Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[N:6][CH:7]=1.[NH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>>[N:11]12[CH2:16][CH2:15][CH:14]([CH2:13][CH2:12]1)[CH:9]([O:8][C:5]1[N:6]=[CH:7][C:2]([C:22]3[CH:23]=[C:18]([CH:19]=[CH:20][CH:21]=3)[NH2:17])=[CH:3][CH:4]=1)[CH2:10]2

Participants

Reactant 2

HCID 922693-Aminophenylboronic acid

HCID 67069920HCID 67069920, compound

Product 1

HCID 11437893HCID 11437893, compound

Procedure

The product of Example 12A (283 mg, 1 mmol) was treated with 3-amino-phenylboronic acid (Lancaster, 274 mg, 2.0 mmol) according to the procedure of Example 1B. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.10) as solid (180 mg, yield, 61%). 1H NMR (MeOH-d4, 300 MHz) δ 1.42-1.56 (m, 1H), 1.62-1.88 (m, 2H), 1.99-2.12 (m, 1H), 2.16-2.28 (m, 1H), 2.73-3.04 (m, 5H), 3.40-3.50 (m, 1H), 5.01-5.10 (m, 1H), 6.70 (ddd, J=7.8, 2.7, 0.7 Hz, 1H), 6.84-6.94 (m, 3H), 7.16 (t, J=7.8 Hz, 1H), 7.88 (dd, J=8.5, 2.4 Hz, 1H), 8.29 (d, J=2.6 Hz, 1H) ppm. MS (DCl/NH3) m/z 296 (M+H)+.

Workup

customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.10) as solid (180 mg, yield, 61%)

Sources & evidence

ORD record: ord-c9d1990cbba6403b95013ccc3fa7c195
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07309699B2

Reaction notes

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