[ CAS No. 1021919-24-3 ] {[proInfo.proName]}

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Quality Control of [ 1021919-24-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1021919-24-3 ]

SDS Specification

Alternatived Products of [ 1021919-24-3 ]

Product Details of [ 1021919-24-3 ]

CAS No. :	1021919-24-3	MDL No. :	MFCD18434446
Formula :	C₉H₁₃BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	261.12	Pubchem ID :	-
Synonyms :

Safety of [ 1021919-24-3 ]

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 [ 1021919-24-3 ]

* 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.

Upstream synthesis route of [ 1021919-24-3 ]
Downstream synthetic route of [ 1021919-24-3 ]

[ 1021919-24-3 ] Synthesis Path-Upstream 1~1

1
[ 1021919-24-3 ]
[ 73183-34-3 ]
[ 936250-20-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium acetate In dimethyl sulfoxide at 90℃; for 18 h;	[00612] B. 3-Methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaboroIan-2-yl)-lH- pyrazole. tert-Butyl 4-bromo-3-methyl-lH-pyrazole-l-carboxylate (0.48 g, 1.84 mmol), bis(pinacolato)diboron (0.535 g, 2.1 mmol), dichloro[l,l'- bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.156 g, 0.19 mmol) and potassium acetate (0.56 g, 5.7 mmol) were placed in a sealed tube, in DMSO (5 mL). The system was flushed with nitrogen, sealed and heated to 90 °C for 18 h. The solvent was removed and the desired product isolated using silica gel chromatography (50percent ethyl acetate in hexanes) to afford the title compound (0.2 g, 50 percent yield). MS (ESI) m/z 209.1 [M+l]⁺.

Reference： [1] Patent: WO2008/51493, 2008, A2, . Location in patent: Page/Page column 181
[2] Patent: US2013/123281, 2013, A1, . Location in patent: Paragraph 0127

[ 1021919-24-3 ] Synthesis Path-Downstream 1~3

1
[ 13808-64-5 ]
[ 24424-99-5 ]
[ 1021919-24-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; In 1,4-dioxane; at 20℃;	A. tert-Butyl 4-bromo-3-methyl-lH-pyrazole-l-carboxylate. 4-Bromo-3- methyl-l H-pyrazole ( 0.3 g, 1.86 mmol), di-t-butyl dicarbonate( 0.65 g, 2.98 mmol) and sodium hydroxide (0.082 g, 2.05 mmol) were placed in 1,4-dioxane (10 mL) and stirred at room temperature overnight. The solvent was removed and the residue treated with ethyl EPO <DP n="185"/>acetate and filtered. The filtrate was concentrated to yield the title compound (0.48 g, 100 % yield). MS (ESI) m/z 261.3 [M]+, 263.3 [M+2]+.
	With sodium carbonate; In dichloromethane; water; for 2.5h;	Step A: N-Boc-4-bromo-3-methyl-pyrazole. To 4-bromo-3-methyl-pyrazole (3.50 g, 21.7 mmol) was added CH2Cl2 (30 mL), di-tert-butyl dicarbonate (5.22 g, 23.9 mmol) and aq Na2CO3 (1 M, 43.5 mL). The reaction was stirred for 2.5 h and the aq portion was then separated. The CH2Cl2 portion was then washed with 5% citric acid followed by brine/saturated aq NaHCO3 (1:1). The solution was dried (Na2SO4), filtered and concentrated to afford the product.
	With sodium carbonate; In dichloromethane; at 20℃; for 16h;	Compound 11 is prepared from compound 10 by reacting (1 eq), Boc2O (1.5 eq), Na2CO3 (2 eq) in DCM at RT for 16 h. After work up and the NMR showed characteristic peaks and was used as such for the next step. In subsequent step compound II (1 eq), and 12 (1.1 eq) in presence of PdCl2(dppf) (0.05 eq), KOAc (3 eq), DMSO was heated to 90 C., 16 h. After column purification LCMS showed 50% of desired mass of compound 11. Key intermediate 14 was prepared was prepared by reacting (1 eq), BH3-DMS (3 eq), THF, RT, 16 h. After work up LCMS showed 96% purity of the compound 14.

0.32 g

With dmap; triethylamine; In acetonitrile; at 20℃;

A mixture of <strong>[13808-64-5]4-bromo-3-methyl-1H-pyrazole</strong> (0.2 g, 1 mmol), di-tert-butyldicarbonate (0.30 g, 1.4 mmol), 4-dimethylaminopyridine (0.02 g, 0.1 mmol) and triethylamine (0.26 mL, 1.9 mmol) in acetonitrile (2 mL) was stirred at rt overnight. The reaction mixture was concentrated, and purified by flash chromatography on a silica gel column eluting with ethyl acetate in hexanes (0-15%) to afford the desired product (0.32 g). LCMS cacld. for C5H6BrN2O2 (M-55)+: m/z=205.0. Found: 204.9.

Reference： [1]Patent: WO2008/51493,2008,A2 .Location in patent: Page/Page column 183-184
[2]Patent: US2008/269279,2008,A1 .Location in patent: Page/Page column 39
[3]Patent: US2013/123281,2013,A1 .Location in patent: Paragraph 0127
[4]Patent: US2014/343030,2014,A1 .Location in patent: Paragraph 0420; 0431; 0432

2
[ 1021919-24-3 ]
[ 73183-34-3 ]
[ 936250-20-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 90℃; for 18h;	[00612] B. 3-Methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaboroIan-2-yl)-lH- pyrazole. tert-Butyl 4-bromo-3-methyl-lH-pyrazole-l-carboxylate (0.48 g, 1.84 mmol), bis(pinacolato)diboron (0.535 g, 2.1 mmol), dichloro[l,l'- bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.156 g, 0.19 mmol) and potassium acetate (0.56 g, 5.7 mmol) were placed in a sealed tube, in DMSO (5 mL). The system was flushed with nitrogen, sealed and heated to 90 C for 18 h. The solvent was removed and the desired product isolated using silica gel chromatography (50% ethyl acetate in hexanes) to afford the title compound (0.2 g, 50 % yield). MS (ESI) m/z 209.1 [M+l]+.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 90℃; for 16h;	Compound 11 is prepared from compound 10 by reacting (1 eq), Boc2O (1.5 eq), Na2CO3 (2 eq) in DCM at RT for 16 h. After work up and the NMR showed characteristic peaks and was used as such for the next step. In subsequent step compound II (1 eq), and 12 (1.1 eq) in presence of PdCl2(dppf) (0.05 eq), KOAc (3 eq), DMSO was heated to 90 C., 16 h. After column purification LCMS showed 50% of desired mass of compound 11. Key intermediate 14 was prepared was prepared by reacting (1 eq), BH3-DMS (3 eq), THF, RT, 16 h. After work up LCMS showed 96% purity of the compound 14.

Reference： [1]Patent: WO2008/51493,2008,A2 .Location in patent: Page/Page column 181
[2]Patent: US2013/123281,2013,A1 .Location in patent: Paragraph 0127

3
[ 1021919-24-3 ]
[ 73183-34-3 ]
[ 1009071-34-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate In dimethyl sulfoxide at 20 - 80℃; for 5.08333h;	35.B Step B: N-Boc-3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazole. To the product of Step A (3.30 g 12.6 mmol) was added bis(pinacolato)diboron (3.53 g, 13.9 mmol), potassium acetate (3.72 g, 37.9 mmol), 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium (II) (0.457 g, 0.632 mmol) and DMSO (15 mL). The reaction vessel was purged with N2 for 5 min at rt prior to heating to 80° C. for about 5 hours. The reaction was cooled to rt, diluted with EtOAc and filtered through Celite. The solution was then washed with brine 5 times and concentrated. The residue was purified by flash chromatography on silica gel gradient eluted with 0-21% EtOAc in hexane affording the title compound. HPLC/MS: 309.3 (M+1); Rt=3.48 min.
	With potassium acetate In 1,2-dimethoxyethane at 90℃; Inert atmosphere;	108.3 A mixture of tert-butyl 4-bromo-3-methyl-lH-pyrazole- 1-carboxylate (9.2 g, 35.2 mmol), 4, 4, 4' , 4' , 5, 5, 5' , 5' - octamethyl-2, 2' -bi-1, 3, 2-dioxaborolane (9.39 g, 37.0 mmol), potassium acetate (10.4 g, 106 mmol) and 1,2-dimethoxyethane (100 itiL) was purged with argon. Then, 1,1'- bis (diphenylphosphino) ferrocenepalladium (II) dichloride dichloromethane adduct (2.88 g, 3.52 mmol) was added, and the mixture was purged with argon again. The mixture was stirred at 900C overnight. After cooled to room temperature, the mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was suspended in 1:1 EtOAc/hexane and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to 70:30 hexane/EtOAc) to afford the crude title compound (7.0 g, 65%) as a colorless oil:1H NMR (300 MHz, CDCl3) δ 1.32 (12H, s) , 1.62 (9H, s) , 2.42 (3H, s), 8.26 (IH, s) . This material included some impurities and was used in next reaction without further purification

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2008/269279, 2008, A1 Location in patent: Page/Page column 39
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2010/101302, 2010, A1 Location in patent: Page/Page column 203-204

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[ CAS No. 1021919-24-3 ] {[proInfo.proName]}

Quality Control of [ 1021919-24-3 ]

Related Doc. of [ 1021919-24-3 ]

Product Details of [ 1021919-24-3 ]

Safety of [ 1021919-24-3 ]

Application In Synthesis of [ 1021919-24-3 ]

[ 1021919-24-3 ] Synthesis Path-Upstream 1~1

[ 1021919-24-3 ] Synthesis Path-Downstream 1~3

Precautionary Statements-General

Prevention

Response

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Disposal

Physical hazards

Health hazards

Environmental hazards

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