Phenylacetylene → HCID 178516877, compound

HRID 539542Notes

Reaction equation

HRID 539542 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][CH2:14]CCN1C=CC=C(OCC2C=CC=CC=2)C1=O)=[N+:10]=[N-:11].[C:32]1([N:38]2[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][C:46]3N=NN[CH:50]=3)=[C:40]([O:51]C)[C:39]2=[O:53])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[C:32]1([N:38]2[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][CH2:46][CH2:50][CH2:14][C:13]3[N:11]=[N:10][NH:9][CH:12]=3)=[C:40]([O:51][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:39]2=[O:53])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 711397661-(5-Azidopentyl)-3-benzyloxypyridine-2-oneHCID 178488794HCID 178488794, compound

Product 1

HCID 178516877HCID 178516877, compoundYield 72%

Procedure

Reaction of phenylacetylene (0.04 g, 0.32 mmol) and 157d (0.10 g, 0.32 mmol) within 4 h as described for synthesis of 158a gave compound 158d (0.092 g, 72%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.78 (m, 3H), 7.30 (m, 8H), 6.79 (d, J=6.8 Hz, 1H), 6.57 (d, J=7.3 Hz, 1H), 5.94 (t, J=7.1 Hz, 1H), 5.02 (s, 2H), 4.31 (t, J=7.0 Hz, 2H), 3.87 (t, J=7.2 Hz, 2H), 1.91 (m, 2H), 1.74 (m, 2H), 1.30 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 157.80, 148.57, 147.39, 136.02, 130.44, 128.64, 128.56, 128.27, 127.81, 127.71, 127.05, 125.40, 119.57, 115.12, 104.49, 70.40, 49.71, 49.06, 29.42, 28.03, 23.05.

Sources & evidence

ORD record
ord-a096c555c0934d558797fd0ec0d56f68
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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