Trimethylsilylacetylene → HCID 86661617, compound

HRID 1496936Notes

Reaction equation

HRID 1496936 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][C@@H:10]2[CH2:15][O:14][C:13]3=[N:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][N:12]3[CH2:11]2)=[CH:4][CH:3]=1.[C:22]([Si](C)(C)C)#[CH:23].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[C:22]([C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][C@@H:10]2[CH2:15][O:14][C:13]3=[N:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][N:12]3[CH2:11]2)=[CH:4][CH:3]=1)#[CH:23]

Participants

4

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 2724141Tetrabutylammonium FluorideHCID 49852039HCID 49852039, compound

Product 1

HCID 86661617HCID 86661617, compoundYield 57.2%

Procedure

Sonogashira coupling of bromide 52 (see Example 2F) (0.310 g, 0.873 mmol) and ethynyltrimethylsilane (0.61 mL, 4.3 mmol) at room temperature for 18 h, followed by desilylation with TBAF, as in Example 2U, gave (6S)-6-[(6-ethynyl-3-pyridinyl)methoxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (130) (0.150 g, 57%) as a white solid: mp 168-170° C.; 1H NMR [(CD3)2SO] δ 8.51 (d, J=1.6 Hz, 1H), 8.02 (s, 1H), 7.74 (dd, J=8.0, 2.2 Hz, 1H), 7.54 (dd, J=8.0, 0.6 Hz, 1H), 4.73 (d, J=12.6 Hz, 1H), 4.70 (d, J=12.6 Hz, 1H), 4.67 (dt, J=12.3, 2.3 Hz, 1H), 4.47 (d, J=11.9 Hz, 1H), 4.29 (s, 1H), 4.20-4.28 (m, 3H). APCI MS m/z 301 [M+H]+.

Sources & evidence

ORD record
ord-d8ce4115f5a04886a62ca52378828aec
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

Loading…