1,2-Dimethoxyethane → HCID 24891682, compound

HRID 1430185Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[CH2:4][NH:5][C:6]([C:8]1[C:13]([OH:14])=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](C#N)[CH:16]=2)=[CH:10][N:9]=1)=[O:7].C[Si]([N:28]=[N+]=[N-])(C)C.C([Sn](=O)CC[CH2:38][CH3:39])CCC.C[O:42][CH2:43][CH2:44]OC>>[CH3:1][O:2][C:3](=[O:23])[CH2:4][NH:5][C:6]([C:8]1[C:13]([OH:14])=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:28][C:43]([CH:44]3[CH2:39][CH2:38]3)=[O:42])[CH:16]=2)=[CH:10][N:9]=1)=[O:7]

Participants

Reactant 4

HCID 80711,2-Dimethoxyethane

HCID 61221Dibutyltin oxide

HCID 78378Azidotrimethylsilane

HCID 24891633HCID 24891633, compound

Product 1

HCID 24891682HCID 24891682, compound

Conditions

Temperature: 140 °C

Procedure

The following heteroaryl substituted phenyl compound can be prepared from {[5-(3-cyano-phenyl)-3-hydroxy-pyridine-2-carbonyl]-amino}acetic acid methyl ester by treatment with trimethylsilyl azide and di-butyl tin oxide in DME and heating the mixture to 140° C., 150 W, 200 psi in a microwave reactor.

Sources & evidence

ORD record: ord-b81741ed866644bb90cab46ade4c9ef6
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940773B2

Reaction notes

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