[ CAS No. 925180-06-9 ]

Name: 925180-06-9|4-Bromo-1-(3-hydroxypropyl)pyrazole|98%
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Quality Control of [ 925180-06-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 925180-06-9 ]

CAS No. :	925180-06-9	MDL No. :	MFCD06804869
Formula :	C₆H₉BrN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YQLRCJHEXNYUIH-UHFFFAOYSA-N
M.W :	205.05 g/mol	Pubchem ID :	16640644
Synonyms :

Safety of [ 925180-06-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 925180-06-9 ]

* 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 [ 925180-06-9 ]

[ 925180-06-9 ] Synthesis Path-Downstream 1~9

1
[ 2075-45-8 ]
[ 627-18-9 ]
[ 925180-06-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;	3 The synthesis of 3-(4-bromo-lH-pyrazol-l-yl)propan-l-ol (0019-2). To a stirred solution of 0019-1 (2.7 g, 18.2 mmol) in DMF (50 ml) was added 3- bromopropan-l-ol (2.8 g, 20.0 mmol) and K2CO3 (3.8 g, 27.3 mmol). The resulting reaction mixture was stirred for 12 h at rt. Then added water, the aqueous phase was extracted with di chi orom ethane, the combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo , purified by C.C. to give the desired product 0019-2 (1.7 g, yield: 46%) as colorless oil.
	With caesium carbonate In N,N-dimethyl-formamide at 50℃;	7.A Cesium carbonate (1.11 g, 3.40 mmol) and 4-bromo-lH-pyrazole (250 mg, 1.70 mmol) were suspended in DMF (8.5 mL). 3-Bromopropan-l-ol (178 μL, 2.041 mmol) was added and the mixture heated to 500C overnight. The mixture was cooled to room temperature, filtered, and the solvent from the filtrate was evaporated under vacuum to give a residue. The residue was purified by column chromatography (gradient: 0 to 2.5% methanol in dichloromethane) to give the title compound. MS [M+H] found 205. 1H NMR (400 MHz, CHLOROFORM-J) δ ppm 2.06 (quin, 2 H), 2.33 (quin, J=6.32 Hz, 1 H), 3.65 (br. s., 1 H), 4.21 - 4.32 (m, 2 H), 4.34 (t, J=6.06 Hz, 1 H), 4.88 (br. s., 1 H), 7.41 - 7.52 (m, 2 H).
	With caesium carbonate In N,N-dimethyl-formamide at 50℃;	98.A Cesium carbonate (1.11 g, 3.40 mmol) and 4-bromo-l/f-pyrazole (250 mg, 1.70 mmol) were suspended in DMF (8.5 rnL). 3-Bromopropan-l-ol (178 μL, 2.041 mmol) was added and heated to 500C overnight. The mixture was cooled to room temperature, filtered, and solvent from the filtrate was evaporated under vacuum to give a residue. The residue was purified by column chromatography (gradient: 0 to 2.5% methanol in dichloromethane) to give the title compound. MS [M+H] found 205. 1H NMR (400 MHz, CHLOROFORM- d) δ ppm 2.06 (quin, 2 H), 2.33 (quin, J=6.32 Hz, 1 H), 3.65 (br. s., 1 H), 4.21 - 4.32 (m, 2 H), 4.34 (t, J=6.06 Hz, 1 H), 4.88 (br. s., 1 H), 7.41 - 7.52 (m, 2 H)

Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA; SHANGPHARMA INNOVATION INC; SHANGPHAMA INNOVATION - WO2020/172324, 2020, A1 Location in patent: Paragraph 0646; 0756-0758
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2010/129848, 2010, A2 Location in patent: Page/Page column 25
[3]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2010/129848, 2010, A2 Location in patent: Page/Page column 70-71

2
[ 925180-06-9 ]
[ 73183-34-3 ]
[ 1000802-50-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 120℃; for 2h; Microwave irradiation;	121 Preparation of intermediate 145: 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H- pyrazol-1-yl]propan-1-ol To a solution of 4-bromo-1-(3-hydroxypropyl)-1H-pyrazole (0.410 g, 2.0 mmol) in dioxane (4 mL) was added at RT bis(pinacolato)diboron (0.609 g, 2.4 mmol), KOAc (0.589 g, 6.0 mmol) and PdCl2(dppf).DCM (0.082 g, 0.1 mmol). The resulting reaction mixture was stirred under microwave irradiation at 100°C for 2 h. The residue was diluted with water and extracted with ethyl acetate twice. The combined organic layer was dried over anhydrous sodium sulfate affording 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol 145 as a brown oil, which was used in the next step without further purification. Yield: 0.504 g of intermediate 145 (quantitative) LCMS method F: [M+H]+ = 253.2, tR = 1.91 min
100%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 120℃; for 2h; Microwave irradiation;	121 Preparation of intermediate 145: 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H- pyrazol-1-yl]propan-1-ol To a solution of 4-bromo-1-(3-hydroxypropyl)-1H-pyrazole (0.410 g, 2.0 mmol) in dioxane (4 mL) was added at RT bis(pinacolato)diboron (0.609 g, 2.4 mmol), KOAc (0.589 g, 6.0 mmol) and PdCl2(dppf).DCM (0.082 g, 0.1 mmol). The resulting reaction mixture was stirred under microwave irradiation at 100°C for 2 h. The residue was diluted with water and extracted with ethyl acetate twice. The combined organic layer was dried over anhydrous sodium sulfate affording 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol 145 as a brown oil, which was used in the next step without further purification. Yield: 0.504 g of intermediate 145 (quantitative) LCMS method F: [M+H]+ = 253.2, tR = 1.91 min
	With sodium acetate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	7.B; 98.B PdCl2(dppf) (28.7 mg, 0.039 mmol), sodium acetate (193 mg, 2.355 mmol), 3-(4- bromo-l/f-pyrazol-l-yl)propan-l-ol (161 mg, 0.785 mmol) and 4,4,4',4',5,5,5',5'- octamethyl-2,2'-bi(l,3,2-dioxaborolane) (598 mg, 2.355 mmol) were added to an oven- dried Schlenk flask. The solids were subjected to 4 cycles of nitrogen and vacuum. DMF (10.5mL) was added and the mixture was heated to 800C overnight. The reaction mixture was cooled to room temperature, filtered, and the filtrate was purified by mass-triggered HPLC (gradient: 25 to 30% ACN in water containing 0.05% TFA) to give the title compound. MS [M+H] found 253

Reference： [1]Current Patent Assignee: SERVIER MONDE; BANQUE DE VIZILLE; CRÉDIT INDUSTRIEL ET COMMERCIAL - CIC - WO2021/224320, 2021, A1 Location in patent: Page/Page column 265-266
[2]Current Patent Assignee: SERVIER MONDE; BANQUE DE VIZILLE; CRÉDIT INDUSTRIEL ET COMMERCIAL - CIC - WO2021/224320, 2021, A1 Location in patent: Page/Page column 265-266
[3]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2010/129848, 2010, A2 Location in patent: Page/Page column 25

3
[ 925180-06-9 ]
[ 1254836-92-4 ]
[ 1254837-92-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In 1,4-dioxane at 115℃; for 0.25h; microwave tube;	98.C PdCl2(dppf) (4.60 mg, 6.28 μmol), N-(4-bromo-2-(trifluoromethoxy)benzyl)-2,6- dioxo-1 -(pyridin-2-ylmethyl)- 1,2, 3, 6-tetrahydropyrimidine-4-carboxamide (62.7 mg, 0.126 mmol), 3-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazol-l-yl)propan- l-ol (38 mg, 0.151 mmol) were suspended in dioxane (628 μL) and sodium bicarbonate (sat., 628 μL) in a microwave tube. The tube was capped and was heated in the microwave to 115°C for 15 minutes. Solvent was evaporated under vacuum to give a residue, which was sonicated with methanol (2 mL) and filtered. The filtrate was purified by mass- triggered HPLC (gradient: 20 to 25% ACN in water containing 0.05% TFA) to give the title compound. MS [M+H] found 545.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2010/129848, 2010, A2 Location in patent: Page/Page column 71

4
[ 925180-06-9 ]
[ 1257996-05-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 0.75 h / 100 °C / Microwave irradiation 2.1: hydrogen / palladium 10% on activated carbon / ethanol; water / 2 h / 20 °C 3.1: trifluoroacetic acid / 2,2,2-trifluoroethanol / 1 h / 105 °C / Microwave irradiation 3.2: 2 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - WO2012/74951, 2012, A1

5
[ 925180-06-9 ]
[ 1380302-86-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 0.75 h / 100 °C / Microwave irradiation 2.1: hydrogen / palladium 10% on activated carbon / ethanol; water / 2 h / 20 °C 3.1: trifluoroacetic acid / 2,2,2-trifluoroethanol / 1 h / 105 °C / Microwave irradiation 3.2: 2 h / 0 - 20 °C 4.1: sodium iodide / butanone / 7 h / 120 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - WO2012/74951, 2012, A1

6
[ 925180-06-9 ]
[ 1257998-32-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 0.75 h / 100 °C / Microwave irradiation 2: hydrogen / palladium 10% on activated carbon / ethanol; water / 2 h / 20 °C

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - WO2012/74951, 2012, A1

7
[ 925180-06-9 ]
[ 1380302-85-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 0.75 h / 100 °C / Microwave irradiation 2.1: hydrogen / palladium 10% on activated carbon / ethanol; water / 2 h / 20 °C 3.1: trifluoroacetic acid / 2,2,2-trifluoroethanol / 1 h / 105 °C / Microwave irradiation 3.2: 2 h / 0 - 20 °C 4.1: sodium iodide / butanone / 7 h / 120 °C / Microwave irradiation 5.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 72 h

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - WO2012/74951, 2012, A1

8
[ 925180-06-9 ]
[ 1257996-65-8 ]
[ 1257998-33-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.75h; Microwave irradiation;	1 Compound 1 D: 4-[1 -(3-Hydroxypropyl)-1 H-pyrazol-4-yl]-2-methyl-7-nitro-2,3-dihydro-1 H- isoindol-1 -oneA suspension of 2-methyl-7-nitro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3- dihydro-1 /-/-isoindol-1-one (Compound 11, 1.825 g, 5.736 mmol), 3-(4-bromo-1 /-/-pyrazol-1 - yl)propan-1 -ol (1 .45 g, 7.07 mmol), [1 ,1 - bis(diphenylphosphino)ferrocene]dichloropalladium(ll), complex with dichloromethane (1 :1 ) (510 mg, 0.62 mmol), and potassium carbonate (2.4 g, 17.3 mmol) in dioxane (20 mL) and H20 (5 mL) was irradiated in a microwave reactor for 45 min at 100 °C. The reaction mixture was poured into water and extracted with CH2CI2 three times. The combined organic layers were washed with brine, dried over anhydrous Na2S04, filtered, concentrated in vacuo, and purified using a Teledyne ISCO CombiFlash Rf system (eluting with 0-15% MeOH:CH2CI2) to isolate the desired compound as 920 mg as a yellow solid. 1H NMR (400 MHz, DMSO-c/6) δ 8.35 (s, 1 H), 8.05 (s, 1 H), 7.99 (d, J = 8.3 Hz, 1 H), 7.88 (d, J = 8.3 Hz, 1 H), 4.72 (s, 2H), 4.63 (t, J = 5.1 Hz, 1 H), 4.25 (t, J = 7.1 Hz, 2H), 3.43 (q, J = 6.1 Hz, 2H), 3.1 1 (s, 3H), 1 .98 (quin, J = 6.6 Hz, 2H). HRMS (ESI): m/z 317.1 1 [M+H]+. UPLC: iR = 0.91 min (UPLC-TOF: polar_3min).

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - WO2012/74951, 2012, A1 Location in patent: Page/Page column 35

9
[ 480424-93-9 ]
[ 925180-06-9 ]
N-(3-(1-(3-hydroxypropyl)-1H-pyrazol-4-yl)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 5h;	3 The synthesis of N-(3-(l-(3-hydroxypropyl)-lH-pyrazol-4-yl)phenyl)acetamide To a stirred solution of compound 0019-2 (240 mg, 1.2 mmol) in dioxane/water (10 mL/2 mL) was added 0015-5 (305 mg, 1.2 mmol), K2CO3 (484 mg, 3.5 mmol), Pd(dppf)Cl2 (80 mg). The resulting reaction mixture was heated to 100 °C and stirred for 5 h and concentrated in vacuo to remove the solvent, then added water, the aqueous phase was extracted with dichloromethane, the combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated, the crude was purified by prep-HPLC to give the desired product SU20666-0019 (49 mg, yield: 16%) as a white solid.[0761] LC-MS (Agilent LCMS 1200-6120, Column: Waters X-Bridge C18 (50 mm4.6 mm3.5 pm); Column Temperature: 40 °C; Flow Rate: 2.0 mL/min; Mobile Phase: from95% [water + 10 mM NH4HCO3] and 5% [CH3CN] to 0% [water + 10 mM NH4HCO3] and 100% [CH3CN] in 1.6 min, then under this condition for 1.4 min, finally changed to 95% [water + 10 mM NH4HCO3] and 5% [CH3CN] in 0.1 min and under this condition for 0.7 min), Purity: 95.43%, Rt = 1.389 min; MS Calcd. : 259.1; MS Found: 260.2 [M+H]+. [0762] HPLC (Agilent HPLC 1200, Column: Waters X-Bridge C18 (150 mm4.6 mm3.5 pm); Column Temperature: 40 °C; Flow Rate: 1.0 mL/min; Mobile Phase: from 95% [water + 10 mM NH4HCO3] and 5% [CH3CN] to 0% [water + 10 mM NH4HCO3] and 100%[CH3CN] in 10 min, then under this condition for 5 min, finally changed to 95% [water + 10 mM NH4HCO3] and 5% [CH3CN] in 0.1 min and under this condition for 5 min), Purity: 99.82%, Rt = 6.418 min.[0763] NMR (400 MHz, DMSO-i) d 1.92-1.97 (2H, m), 2.05 (3H, s), 3.40-3.42 (2H, m), 4.18 (2H, t, J= 6.8 Hz), 4.62 (1H, t, J = 5.2 Hz), 7.21-7.28 (2H, m), 7.38 (1H, d, J = 7.2 Hz), 7.74-7.76 (2H, m), 8.07 (1H, s), 9.93 (1H, s).

Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA; SHANGPHARMA INNOVATION INC; SHANGPHAMA INNOVATION - WO2020/172324, 2020, A1 Location in patent: Paragraph 0646; 0756; 0759-0763

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P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 925180-06-9 ]

Quality Control of [ 925180-06-9 ]

Related Doc. of [ 925180-06-9 ]

Product Details of [ 925180-06-9 ]

Safety of [ 925180-06-9 ]

Application In Synthesis of [ 925180-06-9 ]

[ 925180-06-9 ] Synthesis Path-Downstream 1~9

Related Functional Groups of [ 925180-06-9 ]

Bromides

Alcohols

Related Parent Nucleus of [ 925180-06-9 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 925180-06-9 ]

Related Parent Nucleus of
[ 925180-06-9 ]