944401-67-6|6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine| Ambeed

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CAS No. :	944401-67-6
Formula :	C₁₁H₁₆BFN₂O₂
M.W :	238.07
SMILES Code :	NC1=NC(F)=C(B2OC(C)(C)C(C)(C)O2)C=C1
MDL No. :	MFCD12923416
InChI Key :	URUHDSKWFVRYIP-UHFFFAOYSA-N
Pubchem ID :	59507872

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

Yield	Reaction Conditions	Operation in experiment
35%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 115℃; for 4.25h;Heating / reflux;	0271] To a dry 50-mL flask was added 5-bromo-6-fluoro-2-pyridylamine(370 mg, 1.93 mmol), potassium acetate (569 mg, 5.8 mmol), 4,4,5,5-tetramethyl-2- <n="104"/>(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (538 mg, 2.12 mmol) and dioxane (15 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l'-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloromethane adduct (79 mg, 0.09 mmol). The reaction was refluxed in a 115 C oil bath for 4 hours under argon. After removal of the volatiles in vacuo, EtOAc (150 mL) was added and the solution was washed with H2O (3x40 mL), with NaCl(sat.) (300 mL), dried over Na2SO4, filtered and concentrated. Purification by SiO2 chromatography (30% EtOAc/hexanes) yielded boronate ester (161 mg, 35%). LCMS (m/z): 157 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC) 1H NMR (CDCl3): delta 7.86 (t, J= 8.4 Hz5 IH), 6.29 (dd, J = 8.1, 2.7 Hz, IH), 4.70 (bs, IH), 1.32 (s, 12H).
35%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 115℃; for 4.0h;Inert atmosphere;	Synthesis of 6-fluoro-5-(4,4,5,5-tetramethyl(l,3,2-dioxaborolan-2-yl))-2- pyridylamine[00110] To a dry 50-mL flask was added 5-bromo-6-fluoro-2-pyridylamine (370 mg, 1.93 mmol), potassium acetate (569 mg, 5.8 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (538 mg, 2.12 mmol) and dioxane (15 mL). Argon was bubbled through the solution for 15 minutes, at which timel,l'-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloro methane adduct (79 mg, 0.09 mmol). The reaction was refluxed in a 115 C oil bath for 4 hours under argon. After removal of the volatiles in vacuo, EtOAc (150 mL) was added and the solution was washed with H20 (3x40 mL), with NaCl(sat.) (300 mL), dried over Na2S04, filtered and concentrated. Purification by Si02 chromatography (30% EtOAc/hexanes) yielded boronate ester(161 mg, 35%). LCMS (m/z): 157 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC) ¾ NMR (CDC13): delta 7.86 (t, J= 8.4 Hz, 1H), 6.29 (dd, J= 8.1, 2.7 Hz, 1H), 4.70 (bs, 1H), 1.32 (s, 12H).

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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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Disposal
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CAS No.: 944401-67-6

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CAS No.: 944401-67-6

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[ 944401-67-6 ] Synthesis Path-Downstream 1~1

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed