[ CAS No. 1207623-97-9 ] {[proInfo.proName]}

Name: 1207623-97-9|5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one|97%
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Quality Control of [ 1207623-97-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1207623-97-9 ]

CAS No. :	1207623-97-9	MDL No. :	MFCD16995984
Formula :	C₁₃H₁₇BN₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SQTORENJRGJAKX-UHFFFAOYSA-N
M.W :	260.10	Pubchem ID :	57416440
Synonyms :

Safety of [ 1207623-97-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1207623-97-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1207623-97-9 ]

[ 1207623-97-9 ] Synthesis Path-Downstream 1~14

1
[ 183208-34-6 ]
[ 73183-34-3 ]
[ 1207623-97-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 120℃; for 8h;	To a 0.05 M solution of 5-bromo-l,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (1 equiv) in dioxane was added bis(pinacolato)diboron (1.2 eqiv) and potassium acetate (1.5 equiv) followed by l,r-bis(diphenylphosphino)ferrocene (0.05 equiv). The mixture was degassed with nitrogen for 20 minutes. PdCl2(dppf) (0.05 equiv) was added and the mixture degassed for a further 5 minutes. The reaction was then heated to 120 0C under an inert atmosphere for 8 hours. Upon completion, the reaction was cooled, filtered and concentrated in vacuo to give a crude residue which was purified by flash chromatography (SiO2) using EtOAc/Hexanes - 4:1 as eluent to give the desired product.5-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-l,3-dihydro-pyrrolo[2,3-b]pyridin-2-one: (68 % yield, 92 % purity) m/z (LC-MS,ESP):260 [M-H]- R/T = 3.52 minutes)
30%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 1h;Inert atmosphere;	To a solution of 5-bromo-lH-pyrrolo[2,3-b]pyridin-2(3H)-one (3 g, 14.08 mmol) in 1,4-dioxane (60 mL) were added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (4.29 g, 16.9 mmol), potassium acetate (2.07 g, 21.12 mmol) and l,r-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (1.02 g, 1.41 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 110 C for 1 h. After cooling down the mixture was filtered and the solid was washed with ethyl acetate. The mother liquid was diluted with methanol and the precipitate was filtered and dried in vacuo to afford 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridin-2(3H)-one (1.1 g, 30%): NMR (400 MHz, DMSO-d6) delta 11.14 (s, 1H), 8.29 (s, 1H), 7.68 (s, 1H), 3.54 (s, 2H), 1.29 (s, 12H).
30%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 1h;Inert atmosphere;	Step 3: 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridin-2(3H)-one To a solution of 5-bromo-lH-pyrrolo[2,3-b]pyridin-2(3H)-one (3 g, 14.08 mmol) in 1,4-dioxane (60 mL) were added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (4.29 g, 16.9 mmol), potassium acetate (2.07 g, 21.12 mmol) and l,l'-bis(diphenylphosphino)ferrocene- palladium(II)dichloride (1.02 g, 1.41 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 110 C for 1 h. After cooling down the mixture was filtered and the solid was washed with ethyl acetate. The mother liquid was diluted with methanol and the precipitate was filtered and dried in vacuo to afford 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3- b]pyridin-2(3H)-one (1.1 g, 30%): lU NMR (400 MHz, DMSO-d6) delta 11.14 (s, 1H), 8.29 (s, 1H), 7.68 (s, 1H), 3.54 (s, 2H), 1.29 (s, 12H).

400 mg

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere;

Under an Ar atmosphere, a mixture of <strong>[183208-34-6]5-bromo-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one</strong> (3 g, 14.08 mmol), bis(pinacolato)diboron (5.37 g, 21.1 mmol), Iota , Gamma- bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.206 g, 0.28 mmol) and AcOK (4.14 g, 42 mmol) in DMF was heated at 100 C overnight. After cooling down to the room temperature, the mixture was poured into water. The aqueous layer was extracted with EtOAc, then dried and concentrated. The residue was purified by flash column to give 5-(4,4,5,5-tetramethyl- [l ,3,2]dioxaborolan-2-yl)-l ,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (400 mg) as a yellow solid

Reference： [1]Patent: WO2008/23161,2008,A1 .Location in patent: Page/Page column 111
[2]Patent: WO2014/111496,2014,A1 .Location in patent: Page/Page column 112
[3]Patent: WO2016/142310,2016,A1 .Location in patent: Page/Page column 80
[4]Patent: WO2014/90692,2014,A1 .Location in patent: Page/Page column 47; 48

3
[ 1207623-97-9 ]
[ 1613639-38-5 ]
[ 1613638-68-8 ]

Yield	Reaction Conditions	Operation in experiment
6.5 mg	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 105℃; for 1h; Inert atmosphere; Microwave irradiation;	7.2 Preparation of 5-[5-((R)-2-hydroxy-1-phenyl-ethylamino)-pyridin-3-yl]-1,3- dihydro-pyrrolo [2,3-b] pyridin-2-one Under an Ar atmosphere, a mixture of (R)-2-(5-bromo-pyridin-3-ylamino)-2-phenyl- ethanol (480 mg, 1.644 mmol), 5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro- pyrrolo[2,3-b]pyridin-2-one (468 mg, 1.81 mmol), bis(triphenylphosphine)palladium(II) chloride (232 mg, 0.328 mmol) and potassium carbonate (452 mg, 3.28 mmol) in DMF/H2O (5 : 1 , 10 mL) was exposed to microwave irradiation at 105 °C for 1 hour. Then the mixture was diluted with EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were concentrated and the residue was purified by Prep-HPLC to give 5-[5-((R)-2-hydroxy-1-phenyl- ethylamino)-pyridin-3-yl]-1 ,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (6.5 mg).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2014/90692, 2014, A1 Location in patent: Page/Page column 48

4
[ 183208-32-4 ]
[ 1207623-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid; zinc / 5 h / 20 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 110 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: acetic acid; zinc / 5 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 1 h / 110 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2014/111496, 2014, A1
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2016/142310, 2016, A1

5
[ 271-63-6 ]
[ 1207623-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: bromine; <i>tert</i>-butyl alcohol; water / 16 h / 25 °C 2: acetic acid; zinc / 5 h / 20 °C 3: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 110 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: water; bromine / <i>tert</i>-butyl alcohol / 16 h / 25 °C 2: acetic acid; zinc / 5 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 1 h / 110 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2014/111496, 2014, A1
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2016/142310, 2016, A1

6
[ 1207623-97-9 ]
5-hydroxy-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With oxo(sodioperoxy)borane tetrahydrate In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 1h; Inert atmosphere;	45 A solution of oxo(sodioperoxy)borane tetrahydrate (6.093 g, 39.6 mmol) in H2O (116 mL) was added to a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-pyrrolo[2,3-b] pyridin-2-one (5.15 g, 19.8 mmol) in THF (231 mL) under N2. The reaction mixture was stirred at room temperature for 1 h. Toluene was added and the mixture was evaporated to dryness to give 5-hydroxy-1,3-dihydro-2H -pyrrolo[2,3-b] pyridin-2-one (2.97 g, 100%) as a dark brown solid which was used as such in the next step. LC-MS: C7H6N2O2[M+H]+: 151

Reference： [1]Current Patent Assignee: ALIGOS THERAPEUTICS - WO2022/99066, 2022, A1 Location in patent: Paragraph 00471

7
[ 1207623-97-9 ]
5-(2,6-dichloro-4-nitrophenoxy)-1,3-dihydro-2H -pyrrolo[2,3-b]pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: oxo(sodioperoxy)borane tetrahydrate / tetrahydrofuran; lithium hydroxide monohydrate / 1 h / 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 25 h / 0 - 20 °C / Inert atmosphere