(Pyridin-4-yl)boronic acid → HCID 68542395, compound

HRID 1443065Notes

Reaction equation

HRID 1443065 reaction equation
Br[C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[O:4][CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:6]1[CH2:11][NH:10][C:9](=O)[CH2:8][O:7]1.[N:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>>[C:13]1([C@H:5]([O:4][C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]=2[C:26]2[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=2)[C@H:6]2[O:7][CH2:8][CH2:9][NH:10][CH2:11]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 68539147HCID 68539147, compound

Product 1

HCID 68542395HCID 68542395, compound

Procedure

(S)-2-[(S)-Phenyl-(2-pyridin-4-yl-phenoxy)-methyl]-morpholine was synthesized from 6-[(2-Bromo-phenoxy)-phenyl-methyl]-morpholin-3-one and 4-pyridineboronic acid according to general procedures A and B and was isolated as a thick viscous gum. 1H NMR (CDCl3) δ: 8.65 (d, 2H), 7.60 (d, 2H), 7.32-7.18 (m, 7H), 6.96 (m, 1H), 6.90 (d, 1H), 5.10 (d, 1H), 3.93 (d, 1H), 3.80 (m, 1H), 3.60 (m, 1H), 2.75 (m, 2H), 2.48 (m, 2H), 1.80 (br s, 1H). MS (ES) m/z 347.08 [C22H22N2O2+H]+. Analysis: Calcd for C22H22N2O2:0.5H2O: C, 74.34; H, 6.52; N, 7.88. Found: C, 74.15; H, 6.84; N, 7.37.

Workup

  1. customwas isolated as a thick viscous gum

Sources & evidence

ORD record
ord-8b0e57bf010e40478de68b019bf8776f
Source dataset
uspto-grants-2010_02
Patent number
US07659394B2

Reaction notes

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