4-Fluorophenylboronic acid → HCID 90386031, compound

HRID 2274888Notes

Reaction equation

HRID 2274888 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([NH:12][C:13]([N:15]2[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17][CH2:16]2)=[O:14])([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[C:7]([F:8])=[CH:6][CH:5]=[C:4]([C:9]([NH:12][C:13]([N:15]3[CH:21]4[CH2:20][CH2:19][N:18]([CH2:23][CH2:22]4)[CH2:17][CH2:16]3)=[O:14])([CH3:10])[CH3:11])[CH:3]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 68327753HCID 68327753, compound

Product 1

HCID 90386031HCID 90386031, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Using general procedure E, N-[2-(3-bromo-4-fluorophenyl)propan-2-yl]-1,4-diazabicyclo[3.2.2]nonane-4-carboxamide (100 mg, 0.261 mmol), 4-fluorophenyl boronic acid (91 mg, 0.65 mmol) and palladium (II) acetate gave the title compound as an off-white solid (64 mg, 62%). 1H NMR (400 MHz, CDCl3) δ 7.48 (m, 2H), 7.37-7.30 (m, 2H), 7.10-7.03 (m, 3H), 4.77 (s, 1H), 3.99 (br s, 1H), 3.58 (m, 2H), 3.10-2.90 (m, 6H), 1.98 (m, 2H) 1.71 (m, 8H) ppm. 13C NMR (100 MHz, CDCl3) δ 163.7, 161.3, 159.5, 157.1, 155.6, 144.6, 131.0, 130.9, 127.4, 127.2, 125.7, 116.1, 115.6, 57.9, 55.2, 48.2, 46.4, 46.4, 41.5, 30.6, 30.6, 27.6, 27.6 ppm. Purity: >99% UPLCMS (210 nm); retention time 0.90 min; (M+1) 400.

Sources & evidence

ORD record
ord-9355299c05bc4fee8d87baa22b0563a2
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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