3-Aminophenylboronic acid → 2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxylpyri midin-5-yl}aniline

HRID 970001Notes

Reaction equation

HRID 970001 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][C@@H:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[N:6][CH:7]=1.[NH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>>[N:11]12[CH2:16][CH2:15][CH:14]([CH2:13][CH2:12]1)[C@@H:9]([O:8][C:5]1[N:4]=[CH:3][C:2]([C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH2:17])=[CH:7][N:6]=1)[CH2:10]2

Participants

3

Reactant 2

HCID 922693-Aminophenylboronic acidHCID 67070179(3R)-3-[(5-bromopyrimidin-2-yl)oxy]quinuclidine

Product 1

HCID 865997362-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxylpyri midin-5-yl}aniline

Procedure

The product of Example 19A (280 mg, 1.0 mmol) was coupled with 3-aminophenylboronic acid (Lancaster, 276 mg, 2.0 mmol) according to the procedure of Example 1B. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.1) as a solid (230 mg, yield, 77%). 1H NMR (300 MHz, MeOH-d4) δ 1.48-1.62 (m, 1H), 1.65-1.90 (m, 2H), 2.01-2.15 (m, 1H), 2.21-2.29 (m, 1H), 2.74-3.04 (m, 5H), 3.36-3.47 (m, 1H), 5.12-5.20 (m, 1H), 6.75 (ddd, J=8.2, 2.1, 1.0 Hz, 1H), 6.89 (ddd, J=7.4, 1.7, 1.0 Hz, 1H), 6.93 (t, J=1.8 Hz, 1H), 7.20 (t, J=7.8 Hz, 1H), 8.74 (s, 2H) ppm. MS (DCl/NH3) m/z 297 (M+H)+.

Workup

  1. customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.1) as a solid (230 mg, yield, 77%)

Sources & evidence

ORD record
ord-8b47610274bd40dcba7cbcfa0720172e
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

Loading…