Phenylacetylene → HCID 178516876, compound

HRID 539541Notes

Reaction equation

HRID 539541 reaction equation
[C:1]1([C:7]#C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:9]([CH2:12][CH2:13]CCN1C=CC=C(OCC2C=CC=CC=2)C1=O)=[N+:10]=[N-:11].[C:31]1([N:37]2[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][C:45]3N=NN[CH:49]=3)=[C:39]([O:50]C)[C:38]2=[O:52])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[C:31]1([N:37]2[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][CH2:45][CH2:49][C:13]3[N:11]=[N:10][NH:9][CH:12]=3)=[C:39]([O:50][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:38]2=[O:52])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 711399151-(4-Azidobutyl)-3-benzyloxypyridine-2-oneHCID 178488794HCID 178488794, compound

Product 1

HCID 178516876HCID 178516876, compoundYield 77%

Procedure

Reaction of phenylacetylene (0.124 g, 1.21 mmol) and 157c (0.30 g, 1.01 mmol) within 4 h as described for synthesis of 158a gave compound 158c (0.31 g, 77%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.83 (s, 1H), 7.76 (m, 2H), 7.26 (m, 8H), 6.76 (dd, J=6.9, 1.5 Hz, 1H), 6.56 (dd, J=7.4, 1.5 Hz, 1H), 5.91 (t, J=7.1 Hz, 1H), 4.99 (s, 2H), 4.31 (m, 2H), 3.89 (t, J=7.1 Hz, 2H), 1.85 (m, 2H), 1.67 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 157.71, 148.38, 147.20, 135.83, 130.29, 128.45, 128.41, 128.16, 127.68, 127.63, 126.96, 125.25, 119.87, 114.99, 104.60, 70.26, 49.11, 48.02, 26.78, 25.65. HRMS (EI) calcd for C24H24N4O2 [M]+ 400.1899. found 400.1888.

Sources & evidence

ORD record
ord-1df8213788c14f4e9de9ce52f29b4832
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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