(3-Amino-4-methylphenyl)boronic acid → HCID 11483659, compound

HRID 969971Notes

Reaction equation

I[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.[NH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[CH3:24]>>[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:20]3[CH:21]=[CH:22][C:23]([CH3:24])=[C:18]([NH2:17])[CH:19]=3)=[CH:3][CH:4]=1)[CH2:8]2

Participants

Reactant 2

HCID 2737803(3-Amino-4-methylphenyl)boronic acid

HCID 69434720HCID 69434720, compound

Product 1

HCID 11483659HCID 11483659, compound

Procedure

The product of Example 2A (165 mg, 0.5 mmol), was treated with 3-amino-4-methyl-phenylboronic acid (151 mg, 1 mmol) according to the procedure of Example 2B. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.25) as a solid (104 mg, yield, 68%). 1H NMR (MeOH-d4, 300 MHz) δ 1.45-1.58 (m, 1H), 1.64-1.89 (m, 2H), 2.00-2.13 (m, 1H), 2.15-2.23 (m, 4H), 2.76-3.02 (m, 5H), 3.30-3.40 (m, 1H), 4.51-4.59 (m, 1H), 6.6.84 (dd, J=7.8, 2.0 Hz, 1H), 6.90-6.97 (m, 3H), 7.02 (d, J=7.8 Hz, 1H), 7.47 (dt, J=8.8, 2.0 Hz, 2H) ppm. MS (DCl/NH3) m/z 309 (M+H)+.

Workup

customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.25) as a solid (104 mg, yield, 68%)

Sources & evidence

ORD record: ord-a015ed7826034e8db7e0573b6cc786f4
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07309699B2

Reaction notes

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