Tolylboronic acid → HCID 59166963, compound

HRID 1443077Notes

Reaction equation

[C:1]1([CH:7]([O:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:8]2[CH2:13][NH:12][C:11](=O)[CH2:10][O:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>>[C:1]1([C@H:7]([O:15][C:16]2[C:17]([C:26]3[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][CH:25]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)[C@H:8]2[O:9][CH2:10][CH2:11][NH:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 79799Tolylboronic acid

HCID 68541980HCID 68541980, compound

Product 1

HCID 59166963HCID 59166963, compound

Procedure

(S)-2-[(S)-Phenyl-(2-p-tolyl-pyridin-3-yloxy)-methyl]-morpholine was synthesized from the corresponding amide (6-[Phenyl-(pyridin-3-yloxy)-methyl]-morpholin-3-one) using General Procedure B (employing 4-methylphenylboronic acid in the coupling step) and gave 0.20 g of light brown oil. Two chromatographies of the reaction product on silica gel (eluent—3:1 ethyl acetate/methanol) gave 0.080 g (35%) of the desired product. 1H NMR (400 MHz, CDCl3) δ8.24 (m, 1H), 7.96 (d, 2H), 7.27 (m, 7H), 7.07 (m, 1H), 6.98 (m, 1H), 5.13 (d, 1H), 3.96 (m, 1H), 3.87 (m, 1H), 3.64 (m, 1H), 2.80 (m, 2H), 2.53 (m, 2H), 2.44 (s, 3H). (MS) m/z 361.07 [C23H24N2O2+H+].

Sources & evidence

ORD record: ord-7c7d8fcd0e7a4104bc40439f192cecdb
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659394B2

Reaction notes

Loading…