(2-Methylpropyl)boronic acid → HCID 131733403, compound

HRID 2274872Notes

Reaction equation

HRID 2274872 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10](=[O:23])[NH:11][C:12]([C:15]1[CH:20]=[C:19](Br)[CH:18]=[CH:17][C:16]=1[F:22])([CH3:14])[CH3:13])[CH2:2]2.[CH3:24][CH:25]([CH3:30])[CH2:26]B(O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:22][C:16]1[CH:17]=[CH:18][C:19]([CH2:24][CH:25]([CH3:30])[CH3:26])=[CH:20][C:15]=1[C:12]([NH:11][C:10](=[O:23])[O:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 2734395(2-Methylpropyl)boronic acidHCID 131733402HCID 131733402, compound

Product 1

HCID 131733403HCID 131733403, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Using general procedure E, 1-azabicyclo[2.2.2]oct-3-yl[2-(5-bromo-2-fluorophenyl)propan-2-yl]carbamate (120 mg, 0.312 mmol), 2-methylpropylboronic acid (79.4 mg, 0.779 mmol) and palladium (II) acetate gave the title as a white solid compound (37 mg, 33%). 1H NMR (400 MHz, CDCl3) δ 7.08 (dd, J=2.0, 8.2 Hz, 1H), 6.95 (d, J=4.9 Hz, 1H), 6.93-6.85 (m, 1H), 5.23 (s, 1H), 4.72-4.52 (m, 1H), 3.20-2.47 (m, 6H), 2.41 (d, J=7.1 Hz, 2H), 1.89-1.76 (m, 1H), 2.02-1.26 (m, 5H), 1.70 (d, J=7.6 Hz, 6H), 0.88 (d, J=6.6 Hz, 6H) ppm. 13C NMR (100 MHz, CDCl3) δ 160.4, 158.0, 137.1, 137.1, 129.2, 129.1, 128.1, 116.2, 116.0, 71.2, 55.8, 54.2, 47.6, 46.7, 45.1, 30.5, 29.9, 28.6, 27.0, 25.6, 24.8, 22.5, 19.8, 19.5 ppm. Purity: 95.0% UPLCMS (210 nm); retention time 1.02 min; (M+1) 363.

Sources & evidence

ORD record
ord-b2207db8d25a4f3994f1b868abd4ed57
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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