1346673-94-6|tert-Butyl 2-(diphenylmethyleneamino)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate| Ambeed

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CAS No. :	1346673-94-6
Formula :	C₂₆H₂₇N₃O₂
M.W :	413.51
SMILES Code :	O=C(OC(C)(C)C)N1CC2=C(CC1)N=C(C=C2)N=C(C3=CC=CC=C3)C4=CC=CC=C4
MDL No. :	MFCD29054177
InChI Key :	UUQHZMNWDMRSTN-UHFFFAOYSA-N
Pubchem ID :	58043757

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Yield	Reaction Conditions	Operation in experiment
33%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 3.08333h;Inert atmosphere;	Nitrogen was bubbled into a solution of compound 37 (1.0 g, 3.7 mmol, 1.0 eq), compound 38 (742 mg, 4.1 mmol, 1.1 eq), Pd2(dba)3 (340 mg, 0.37 mmol, 0.1 eq), Xantphos (454 mg, 0.78 mmol, 0.21 eq) and CS2CO3 (2.4 g, 7.4 mmol, 2 eq) in dioxane (20 mL) for 5 mins. The mixture was stirred at 110 C for 3 h. After completion, the mixture was cooled down to RT, diluted with DCM (50 mL) and filtered through a pad of Celite, rinsed with DCM (20 mL). The filtrate was dried over sodium sulfate, concentrated and purified by silica column to give the desired product as a yellow solid (0.5 g, 33%). NMR (300 MHz, CDCb): delta 7.36-7.25 (m, 10 H), 7.17 (d, J= 8.1 Hz, 1 H), 6.35 (d, J= 8.4 Hz, 1 H), 4.48 (s, 2 H), 3.70 (t, J= 6.0 Hz, 2 H), 2.92 (s, J= 6.0 Hz, 2 H), 1.50 (s, 9 H). LCMS: (M+H)+:413.9.
	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 110℃; for 48h;	To a round-bottomed flask equipped with a stirring bar, tert-butyl 2-chloro-7,8- dihydro-l,6-naphthyridine-6(5H)-carboxylate (1.09 g, 4.05 mmol), diphenyl-methanimine 26 (2.20 g, 12.14 mmol), Pd(OAc)2 (181.6 mg, 0.809 mmol), BINAP (503.8 mg, 0.809 mmol), CS2CO3 (6.59 g, 20.23 mmol) and toluene (16 mL) were added. The reaction mixture was heated at 110 C for 2 days. The reaction mixture was filtered and removed solvent in vacuo. The residue 158a was directly used in the next step.
	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate;	Intermediate W-1 was synthesized through the reaction of <strong>[1151665-15-4]tert-butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate</strong> with benzophenone imine and tert-butoxysodium in the presence of a Pd catalyst and deprotection.

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CAS No.: 1346673-94-6

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CAS No.: 1346673-94-6

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[ 1346673-94-6 ] Synthesis Path-Downstream 1~2

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Physical hazards
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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
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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