1111637-95-6|3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine| Ambeed

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CAS No. :	1111637-95-6
Formula :	C₁₄H₁₉BN₂O₂
M.W :	258.12
SMILES Code :	CC1(C)OB(C2=CN=C(NC=C3C)C3=C2)OC1(C)C
MDL No. :	MFCD12923386

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Yield	Reaction Conditions	Operation in experiment
43%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 80 - 90℃;Inert atmosphere;	To a solution of 5-bromo-3-methyl-lH-pyrrolo[2,3-b]pyridine (20 g, 94.8 mmol) in NN-dimethylformamide (200 mL) was added potassium acetate (27.9 g, 284.4 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (28.8 g, 113.74 mmol). The resulting mixture was degassed with nitrogen for 5 min, l,l'-Bis(diphenylphosphino)ferrocene-palladium(n)dichloride (6.65g, 9.48mmol) was added and the mixture was degassed with nitrogen once more for 5 min. The reaction mixture was stirred overnight at 80-90 C. The reaction mixture was poured into water, extracted with (3 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 9% to 50% ethyl acetate in petroleum ether) affording 3-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine as a white solid (10.5 g, 43%): NMR (400MHz, DMSO-d6), delta 11.360 (s, 1H), 8.371-8.375 (d, /= 1.6 Hz, 1H), 8.097-8.100 (s, /= 1.2 Hz, 2H), 7.17 (s, 1H), 3.296 (s, 3 H), 1.245 (s, 12H).
43%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 80 - 90℃;Inert atmosphere;	Step 7: 3-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine To a solution of 5-bromo-3-methyl-lH-pyrrolo[2,3-b]pyridine (20 g, 94.8 mmol) in N,N- dimethylformamide (200 mL) was added potassium acetate (27.9 g, 284.4 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (28.8 g, 113.74 mmol). The resulting mixture was degassed with nitrogen for 5 min, l,l'-Bis(diphenylphosphino)ferrocene- palladium(II)dichloride (6.65g, 9.48mmol) was added and the mixture was degassed with nitrogen once more for 5 min. The reaction mixture was stirred overnight at 80-90 C. The reaction mixture was poured into water, extracted with (3 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 9% to 50% ethyl acetate in petroleum ether) affording 3-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine as a white solid (10.5 g, 43%): lU NMR (400MHz, DMSO-d6), delta 11.360 (s, 1H), 8.371-8.375 (d, = 1.6 Hz, 1H), 8.097-8.100 (s, = 1.2 Hz, 2H), 7.17 (s, 1H), 3.296 (s, 3 H), 1.245 (s, 12H).
	With potassium acetate;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 80 - 90℃;	Preparation of 3-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrolo[2,3-b]pyridine (B-5-5)To a solution of 5-bromo-3-methyl-1 H-pyrrolo[2,3-b]pyridine (B-5-4) (0.5 g, 2.37 mmol) in DMF (150 mL) were added KOAc (0.7 g, 7.11 mmol) and bis(pinacolato)diboron (0.72 g, 2.84 mmol). The resulting mixture was degassed under N2 for 2 minutes. Then Pd(PPh3J2CI2 (0.2 g, 0.237 mmol) was added and the mixture was degassed again. The reaction was heated to 80-900C and stirred overnight. The mixture was poured into water (30 mL), extracted with EtOAc (15 mLchi3). The organic layer was washed with saturated aqueous NaCI, dried over Na2SO4 and concentrated to give crude 3-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrrolo[2,3-b]pyridine (B-5-5) (0.7 g), which was used directly in next step.

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CAS No.: 1111637-95-6

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CAS No.: 1111637-95-6

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[ 1111637-95-6 ] Synthesis Path-Downstream 1~1

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H200	Unstable explosive
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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
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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