Phenylboronic Acid → HCID 68327942, compound

HRID 2274889Notes

Reaction equation

HRID 2274889 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:23])=[C:6]([C:8]([NH:11][C:12]([N:14]2[CH:20]3[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]3)[CH2:16][CH2:15]2)=[O:13])([CH3:10])[CH3:9])[CH:7]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:23][C:5]1[CH:4]=[CH:3][C:2]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:7][C:6]=1[C:8]([NH:11][C:12]([N:14]1[CH:20]2[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 68327911HCID 68327911, compound

Product 1

HCID 68327942HCID 68327942, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Using general procedure E, N-(2-(5-bromo-2-fluorophenyl)propan-2-yl)-1,4-diazabicyclo[3.2.2]nonane-4-carboxamide (100 mg, 0.261 mmol), phenyl boronic acid (30 mg, 0.25 mmol) and palladium (II) acetate gave the title compound as an off-white solid (27 mg, 39%). 1H NMR (400 MHz, CDCl3) δ 7.56-7.51 (m, 3H), 7.41-7.37 (m, 3H), 7.32-7.30 (m, 1H), 7.03 (m, 1H), 4.90 (s, 1H), 4.00 (br s, 1H), 3.59 (m, 2H), 3.11-2.92 (m, 6H), 2.04-1.98 (m, 2H) 1.78 (s, 6H), 1.73-1.67 (m, 2H) ppm. 13C NMR (100 MHz, CDCl3) δ 161.8, 159.4, 155.9, 140.9, 137.2, 134.6, 128.9, 127.4, 127.3, 127.2, 127.1, 127.0, 116.9, 57.9, 54.4, 48.1, 46.5, 46.5, 41.4, 29.9, 29.3, 27.5, 27.5 ppm. Purity: >99% UPLCMS (210 nm); retention time 0.90 min; (M+1) 400.

Sources & evidence

ORD record
ord-232c2ae7d04f4a5db501deee09c8acac
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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