4-Bromo-1-isopropyl-1H-pyrazole → HCID 58266758, compound

HRID 1505930Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:8]=[N:9][N:10]([CH:12]([CH3:14])[CH3:13])[CH:11]=1.[Cl-].[CH2:16]([SnH:20]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>C(OCC)C>[CH:12]([N:10]1[CH:11]=[C:7]([Sn:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:8]=[N:9]1)([CH3:14])[CH3:13]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (2.5M in hexanes, 1.38 mL, 3.45 mmol) was added over 15 min to a solution of 4-bromo-1-isopropyl-1H-pyrazole (500 mg, 2.65 mmol) in diethyl ether (10 mL) at −78° C. After 30 min, a solution of tri-n-butylstannane chloride (920 μL, 3.45 mmol) in diethyl ether (1 mL) was added and the resultant reaction mixture was left to stir at −78° C. for 1 h, then allowed to warm to ambient temperature. The reaction mixture was diluted with diethyl ether (40 mL) and washed with water (20 mL), then brine (20 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford the title product as a colourless oil (98 mg, 94%) which was used without further purification. 1H NMR (CDCl3, 400 MHz): 7.46-7.42 (m, 1H); 7.28 (t, J=4.2 Hz, 1H); 4.59-4.43 (m, 1H); 1.58-1.42 (m, 12H); 1.39-1.24 (m, 6H); 1.02-0.77 (m, 15H).

Workup

customthe resultant reaction mixture
waitwas left
temperatureto warm to ambient temperature
washwashed with water (20 mL)
customThe organic layer was separated
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-0e56da44c4aa478e9f239eae458292c9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216980B2

Reaction notes

Loading…