3-Nitrophenylboronic Acid → HCID 58020108, compound

HRID 1632068Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20](F)=[N:21][CH:22]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[N+](C1C=C(B(O)O)C=CC=1)([O-])=[O:25].N12[CH2:46][CH2:45][CH2:44][N:43]=[C:42]1CCCCC2>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([N:43]4[CH2:42][CH2:46][CH:45]([OH:25])[CH2:44]4)=[N:21][CH:22]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 5-(3′-chloro-6-methoxy-biphenyl-3-ylmethyl)-2-fluoro-pyridine (I-140, 0.22 g, 0.67 mmol) and 3-pyrrolidinol (2) (0.12 g, 1.34 mmol) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.51 g, 3.36 mmol). The reaction mixture was stirred and heated at 100° C. for 1.5 h, cooled to room temperature, diluted with dichloromethane (8 mL), washed with 0.5 N HCl (2×4 mL), dried with Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography using 5% methanol in dichloromethane to afford 0.13 g (49%) of P-602 as white solid. 1H NMR (DMSO-d6, 400 MHz): 7.9 (d, J=2.4 Hz, 1H), 7.3-7.49 (m, 5H), 7.12-7.2 (m, 2H), 7.03 (d, J=8.4 Hz, 1H), 6.34 (d, J=8.8 Hz, 1H), 4.89 (d, J=3.6 Hz, 1H), 4.35 (br s, 1H), 3.76 (s, 2H), 3.73 (s, 3H), 3.2-3.45 (m, 4H), 1.8-2.05 (m, 2H) ppm; MS (APCI+): 395.1 (M+1), LC-MS: 99.1%.

Workup

temperaturecooled to room temperature
washwashed with 0.5 N HCl (2×4 mL)
dry with materialdried with Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography
customto afford 0.13 g (49%) of P-602 as white solid

Sources & evidence

ORD record: ord-10651b428f004db1b0fee5948737b7b1
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791267B2

Reaction notes

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