1034467-27-0|2-Fluoro-4-iodo-5-(methoxymethoxy)pyridine| Ambeed

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CAS No. :	1034467-27-0
Formula :	C₇H₇FINO₂
M.W :	283.04
SMILES Code :	COCOC1=CN=C(F)C=C1I
MDL No. :	MFCD22123918
InChI Key :	DPHOQZPEXMFCGW-UHFFFAOYSA-N
Pubchem ID :	66738153

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
53%		Preparation 462-Fluoro-4-iodo-5-methoxymethoxy -pyridine Cool a solution of 2-fluoro-5-methoxymethoxy-pyridine (4.1 g, 26.1 mmol) inTHF (60 mL) to -75 0C. Add tert-butyllithium (1.7 M in pentane, 30.4 mL, 51.7 mmol) <n="21"/>over a period of 30 min. Stir the mixture for an additional half an hour. Add iodine (9.8 g, 38.6 mmol, dissolved in 60 mL of THF). Stir for 1 h after the addition is complete. Allow the temperature to raise to RT over 1 h while stirring. Treat the mixture with water. Extract the solution with ethyl acetate three times. Wash the organic layer with aqueous saturated sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown solid. Triturate the brown solid with hexane. Filter to afford the title compound (3.9 g, 53 %) as a brown solid. 1H NMR (400 MHz, CDCl3) delta 3.53 (s, 3H), 5.23 (s, 2H), 7.39 (d, J= 4.0 Hz, 1 H), 7.96 (d, J= 1.6 Hz, IH).
52.8%		Preparation 18; 2-Fluoro-4-iodo-5-methoxymethoxy -pyridine; Cool a solution of 2-fluoro-5-methoxymethoxy-pyridine (4.1 g, 26.1 mmol) inTHF (60 mL) to -75 0C. Add tert-butyllithium (1.7 M in pentane, 30.4 mL, 51.66 mmol) over a period of 30 min. Stir the mixture for an additional half an hour. Add iodine (9.8 g, 38.61 mmol, dissolved in 60 mL of tetrhydrofuran). Stir for 1 hour after the addition is complete. Allow the temperature to rise to room temperature over 1 hour while stirring. Treat the mixture with water. Extract the solution with ethyl acetate three times. Wash the organic layer with saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown solid. Triturate the brown solid with hexane. Filter to afford the title compound (3.9 g, 52.8 %) as a brown solid. 1H NMR (400 MHz, CDCl3) delta 3.53 (s, 3H), 5.23 (s, 2H), 7.39 (d, J= 4.0 Hz, 1 H), 7.96 (d, J = 1.6 Hz, IH).

Yield	Reaction Conditions	Operation in experiment
97.18%		Preparation 19; 6-Fluoro-4-iodo-pyridin-3 -ol; Add HCl (3 M in water, 31 mL, 93.01 mmol) to a solution of 2-fluoro-4-iodo-5- methoxymethoxy-pyridine (3.9 g, 13.78 mmol) in THF (20 mL). Stir the mixture at 60 0C for 3 hours. Cool down the mixture. Adjust the pH to 7 with slow addition of saturated aqueous sodium bicarbonate solution. Extract the solution with ethyl acetate three times. Wash the organic layer with saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to afford the title compound (3.2 g, 97.18 %) as a yellow solid. MS (EI) m/z 240 [M+l]+.
97%		Preparation 476-Fluoro-4-iodo-pyridin-3 -olAdd HCl (3 M in water, 31 mL, 93.0 mmol) to a solution of 2-fluoro-4-iodo-5- methoxymethoxy-pyridine (3.9 g, 13.8 mmol) in THF (20 mL). Stir the mixture at 60 0C for 3 h and cool down the mixture. Adjust the pH to 7 with slow addition of a saturated aqueous sodium bicarbonate solution. Extract the solution with ethyl acetate three times. Wash the organic layer with aqueous saturated sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to afford the title compound (3.2 g, 97 %) as a yellow solid. MS (ES) m/z 240 [M+ 1]+.

2-Fluoro-4-iodo-5-(methoxymethoxy)pyridine

CAS No.: 1034467-27-0

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