Dimethylformamide → HCID 87549645, compound

HRID 1875220Notes

Reaction equation

[Li]CC[CH2:4][CH3:5].Br[C:7]1[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9](Br)=[C:10]([Br:12])[N:11]=1.BrCC.CN([CH:28]=[O:29])C>C1COCC1>[Br:12][C:10]1[N:11]=[C:7]([CH2:4][CH3:5])[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]=1[CH:28]=[O:29]

Participants

Conditions

Temperature: -78 °C

Procedure

n-BuLi (1.42 mL of a 1.6 M solution in hexanes, 2.24 mmol) was added dropwise to a −78° C. solution of 2,4,5-tribromo-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole (0.98 g, 2.24 mmol) in THF (46 mL). The reaction mixture was stirred for 30 min and bromoethane (0.17 mL, 2.24 mmol) was added dropwise. The solution was stirred for 4 h at RT, cooled to −78° C., and n-BuLi (1.42 mL of a 1.6 M solution in hexanes, 2.24 mmol) was added dropwise. After 30 mins, DMF (2 mL, 23.9 mmol) was added. The reaction mixture was allowed to warm to RT, quenched by addition of sat'd NH4Cl and extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and purified by silica gel chromatography (0-70% EtOAc/hex) to afford the title compound (0.16 g, 22%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.69 (s, 1H), 5.70 (s, 2H), 3.50-3.60 (m, 2H), 2.79 (q, J=7.51 Hz, 2H), 1.35 (t, J=7.56 Hz, 3H), 0.78-0.98 (m, 2H), −0.04 (s, 9H).

Workup

stirringThe solution was stirred for 4 h at RT
waitAfter 30 mins
temperatureto warm to RT
customquenched by addition of sat'd NH4Cl
extractionextracted with CH2Cl2
dry with materialThe organic phase was dried (Na2SO4)
filtrationfiltered
custompurified by silica gel chromatography (0-70% EtOAc/hex)

Sources & evidence

ORD record: ord-7b4adbffce5447fe93781e90e8a98260
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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