[ CAS No. 885520-23-0 ] {[proInfo.proName]}

Name: 885520-23-0|6-Bromo-4-fluoro-1H-indazole|98%
Brand: Ambeed
SKU: A237672
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Quality Control of [ 885520-23-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 885520-23-0 ]

Product Details of [ 885520-23-0 ]

CAS No. :	885520-23-0	MDL No. :	MFCD07781444
Formula :	C₇H₄BrFN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IHCPAAHPKILIIC-UHFFFAOYSA-N
M.W :	215.02	Pubchem ID :	24728744
Synonyms :

Calculated chemistry of [ 885520-23-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.75
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	2.34
Log Po/w (WLOGP) :	2.88
Log Po/w (MLOGP) :	2.31
Log Po/w (SILICOS-IT) :	3.13
Consensus Log Po/w :	2.41

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.25
Solubility :	0.12 mg/ml ; 0.000559 mol/l
Class :	Soluble
Log S (Ali) :	-2.58
Solubility :	0.563 mg/ml ; 0.00262 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.05
Solubility :	0.0192 mg/ml ; 0.0000893 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.77

Safety of [ 885520-23-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H317-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 885520-23-0 ]

* 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 [ 885520-23-0 ]
Downstream synthetic route of [ 885520-23-0 ]

[ 885520-23-0 ] Synthesis Path-Upstream 1~5

1
[ 537013-51-7 ]
[ 885520-23-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrazine hydrate In ethylene glycol at 95℃; for 2 h; Inert atmosphere	To a stirred suspension of 4-bromo-2,6-difluorobenzaldehyde 20 (commercially available, CAS 537013-51-7, 442.0 mg, 2.00 mmol) in ethylene glycol (10 mL) at ambient temperature was added hydrazine monohydrate (0.19 mL, 4.00 mmol). The resulting suspension was heated to 95 C under nitrogen for 2 h.The reaction was then cooled to 5 C and diluted with water. The solution was extracted with ethyl acetate, dried over anhydrous Na2SO4, and concentrated to yield 6-bromo-4-fluoro-1H-indazole 21 (430.0 mg, 100percent) as a yellow solid.
71%	With hydrazine hydrate In 1,4-dioxane at 95℃; for 1.5 h;	A mixture of 4-bromo-2,6-difluorobenzaldehyde (50 g, 226 mmol) and N₂H₄-H₂O (100 mL) in 1,4-dioxane (100 mL) was heated to 95° C. and stirred at this temperature for 1.5 h. After being cooled to r.t., the reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was dried and concentrated to give 6-bromo-4-fluoro-1H-indazole (35 g, 163 mmol, 71percent) as a yellow solid, which was used for the next step without any further purification.

Reference： [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 23, p. 6194 - 6205
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 3187 - 3197
[3] Patent: US2015/99782, 2015, A1, . Location in patent: Paragraph 0225; 0226

2
[ 1227912-19-7 ]
[ 885520-23-0 ]

Yield	Reaction Conditions	Operation in experiment
41%	With hypophosphorous acid; isopentyl nitrite In ethanol at 0 - 20℃;	To a suspension of 6-bromo-4-fluoro-lH-indazol-3 -amine (i-9b) (25 g, 108.7 mmol) in anhydrous ethanol (400 mL) was added H₃P0₂ (74.4 g, 563.6 mmol) and cooled to 0 °C. To the reaction mixture was added isoamyl nitrite (15.24 g, 130.3 mmol), and the mixture was warmed to room temperature and stirred for 2 h. To the resulting brown suspension was added an additional amount of isoamyl nitrite (8 g, 68.3 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with brine (500 mL) and filtered. The filtrate was extracted with ethyl acetate (500 mL x 3). The combined organic layers were dried over anhydrous MgS0_4, filtered and concentrated in vacuum. The crude product was purified by column chromatography on silica gel (PE / EtOAc = 15 / 1 to 5 / 1) to obtain the title compound (9.7 g, yield: 41percent) as a yellow solid. LCMS (ESI) calc'd for C₇H₄BrFN₂ [M+H]⁺: 215, found: 215.
41%	With hypophosphorous acid; isopentyl nitrite In ethanol at 0 - 20℃;	ii). Preparation of 6-bromo-4-fluoro-1H-indazole (i-9c) To a suspension of 6-bromo-4-fluoro-1H-indazol-3-amine (i-9b) (25 g, 108.7 mmol) in anhydrous ethanol (400 mL) was added H₃PO₂ (74.4 g, 563.6 mmol) and cooled to 0° C. To the reaction mixture was added isoamyl nitrite (15.24 g, 130.3 mmol), and the mixture was warmed to room temperature and stirred for 2 h. To the resulting brown suspension was added an additional amount of isoamyl nitrite (8 g, 68.3 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with brine (500 mL) and filtered. The filtrate was extracted with ethyl acetate (500 mL*3). The combined organic layers were dried over anhydrous MgSO₄, filtered and concentrated in vacuum. The crude product was purified by column chromatography on silica gel (PE/EtOAc=15/1 to 5/1) to obtain the title compound (9.7 g, yield: 41percent) as a yellow solid. LCMS (ESI) calc'd for C₇H₄BrFN₂ [M+H]⁺: 215. found: 215.

Reference： [1] Patent: WO2014/28591, 2014, A2, . Location in patent: Page/Page column 51
[2] Patent: US2015/210687, 2015, A1, . Location in patent: Paragraph 0262

3
[ 886761-86-0 ]
[ 885520-23-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 10, p. 4458 - 4473

4
[ 123843-67-4 ]
[ 885520-23-0 ]

Reference： [1] Patent: WO2014/28591, 2014, A2,
[2] Patent: US2015/210687, 2015, A1,

5
[ 67-56-1 ]
[ 885520-23-0 ]
[ 201230-82-2 ]
[ 885521-44-8 ]

Yield	Reaction Conditions	Operation in experiment
48.3%	at 70℃; for 16 h;	To a solution of 6-bromo-4-fluoro-lH-indazole (i-9c) (6.5 g, 0.03 mol) in 130 mL of methanol were added Pd(dppf)Cl₂ (0.37 g, 0.005 mol) and triethylamine (6.15 g, 0.06 mol). Then the mixture was stirred at 70 °C under 50 psi of CO for 16 h. The mixture was filtered and the filtrate was concentrated. The crude residue was purified by column chromatography on silica gel eluted with (PE / EtOAc = 5 : 1) to afford the title compound (2.8 g, yield: 48.3percent) as a pale yellow solid. LCMS (ESI) calc'd for C₉H₇FN₂0₂ [M+H]⁺: 195, found: 195.
48.3%	at 70℃; for 16 h;	iii). Preparation of methyl 4-fluoro-1H-indazole-6-carboxylate (i-9d) To a solution of 6-bromo-4-fluoro-1H-indazole (i-9c) (6.5 g, 0.03 mol) in 130 mL of methanol were added Pd(dppf)Cl₂ (0.37 g, 0.005 mol) and triethylamine (6.15 g, 0.06 mol). Then the mixture was stirred at 70° C. under 50 psi of CO for 16 h. The mixture was filtered and the filtrate was concentrated. The crude residue was purified by column chromatography on silica gel eluted with (PE/EtOAc=5:1) to afford the title compound (2.8 g, yield: 48.3percent) as a pale yellow solid. LCMS (ESI) calc'd for C₉H₇FN₂O₂ [M+H]⁺: 195. found: 195.

Reference： [1] Patent: WO2014/28591, 2014, A2, . Location in patent: Page/Page column 51
[2] Patent: US2015/210687, 2015, A1, . Location in patent: Paragraph 0264

[ 885520-23-0 ] Synthesis Path-Downstream 1~88

1
[ 885520-23-0 ]
[ 2550-36-9 ]
[ 937047-78-4 ]

Yield	Reaction Conditions	Operation in experiment
32%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;	To a mixture of 6-bromo-4-f luoro-1 H-indazole (2.0 g, 10.15 mmol) and K2CO3 (7.01 g, 50.75 mmol) in DMF (16 mL) was added cyclohexylmethyl bromide (3.67 g, 20.30 mmol) and the mixture was stirred at rt for 18 h. The mixture was diluted with ethyl acetate and washed successively with water and saturated, aqueous NaHCO3, then dried over MgSO4 and concentrated. The product (0.97 g, 32%) was isolated using an ISGO instrument using 0 -15 % ethyl acetate in hexanes. LC-MS [M+H]+ = 293.3, 295.1 , RT = 4.04 min.

Reference： [1]Patent: WO2007/56170,2007,A2 .Location in patent: Page/Page column 124

2
[ 885520-23-0 ]
[ 100-39-0 ]
[ 937047-77-3 ]

Yield	Reaction Conditions	Operation in experiment
36%		A mixture of 6-bromo-4-fluoro-1 H-indazole (0.5 g, 2.26 mmol) and benzyl bromide (0.55 g, 3.16 mmol) in 1,4-dioxane (10 mL) was stirred at reflux for 18 h. DMF (5 mL) and NaHCO3 (0.95 g, 11.28 mmol) were added to the mixture and heating continued at 100 C for 18 h. The mixture was diluted with ethyl acetate and subsequently washed with <n="126"/>water and brine, dried over MgSO4 and concentrated. The product (0.25 g, 36%) was isolated using an ISCO instrument using 0 -10 % ethyl acetate in hexanes. LC-MS [M+Hf = 305.4, 307.0, RT = 3.81 min.

Reference： [1]Patent: WO2007/56170,2007,A2 .Location in patent: Page/Page column 123-124

3
[ 123843-67-4 ]
[ 885520-23-0 ]

Reference： [1]Patent: WO2014/28591,2014,A2
[2]Patent: US2015/210687,2015,A1

4
[ 1227912-19-7 ]
[ 885520-23-0 ]

Yield	Reaction Conditions	Operation in experiment
41%	With hypophosphorous acid; isopentyl nitrite; In ethanol; at 0 - 20℃;	To a suspension of 6-bromo-4-fluoro-lH-indazol-3 -amine (i-9b) (25 g, 108.7 mmol) in anhydrous ethanol (400 mL) was added H3P02 (74.4 g, 563.6 mmol) and cooled to 0 C. To the reaction mixture was added isoamyl nitrite (15.24 g, 130.3 mmol), and the mixture was warmed to room temperature and stirred for 2 h. To the resulting brown suspension was added an additional amount of isoamyl nitrite (8 g, 68.3 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with brine (500 mL) and filtered. The filtrate was extracted with ethyl acetate (500 mL x 3). The combined organic layers were dried over anhydrous MgS04, filtered and concentrated in vacuum. The crude product was purified by column chromatography on silica gel (PE / EtOAc = 15 / 1 to 5 / 1) to obtain the title compound (9.7 g, yield: 41%) as a yellow solid. LCMS (ESI) calc'd for C7H4BrFN2 [M+H]+: 215, found: 215.
41%	With hypophosphorous acid; isopentyl nitrite; In ethanol; at 0 - 20℃;	ii). Preparation of 6-bromo-4-fluoro-1H-indazole (i-9c) To a suspension of <strong>[1227912-19-7]6-bromo-4-fluoro-1H-indazol-3-amine</strong> (i-9b) (25 g, 108.7 mmol) in anhydrous ethanol (400 mL) was added H3PO2 (74.4 g, 563.6 mmol) and cooled to 0 C. To the reaction mixture was added isoamyl nitrite (15.24 g, 130.3 mmol), and the mixture was warmed to room temperature and stirred for 2 h. To the resulting brown suspension was added an additional amount of isoamyl nitrite (8 g, 68.3 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with brine (500 mL) and filtered. The filtrate was extracted with ethyl acetate (500 mL*3). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuum. The crude product was purified by column chromatography on silica gel (PE/EtOAc=15/1 to 5/1) to obtain the title compound (9.7 g, yield: 41%) as a yellow solid. LCMS (ESI) calc'd for C7H4BrFN2 [M+H]+: 215. found: 215.

Reference： [1]Patent: WO2014/28591,2014,A2 .Location in patent: Page/Page column 51
[2]Patent: US2015/210687,2015,A1 .Location in patent: Paragraph 0262

5
[ 885520-23-0 ]
[ 1562195-50-9 ]

Reference： [1]Patent: WO2014/28591,2014,A2
[2]Patent: US2015/210687,2015,A1

6
[ 885520-23-0 ]
[ 1562195-54-3 ]

Reference： [1]Patent: WO2014/28591,2014,A2
[2]Patent: US2015/210687,2015,A1

7
[ 885520-23-0 ]
[ 1562195-58-7 ]

Reference： [1]Patent: WO2014/28591,2014,A2
[2]Patent: US2015/210687,2015,A1

8
[ 885520-23-0 ]
[ 1562397-95-8 ]

Reference： [1]Patent: WO2014/28591,2014,A2
[2]Patent: US2015/210687,2015,A1

9
[ 885520-23-0 ]
[ 1562194-20-0 ]

Reference： [1]Patent: WO2014/28591,2014,A2
[2]Patent: US2015/210687,2015,A1

10
[ 885520-23-0 ]
[ 885521-35-7 ]

Reference： [1]Patent: WO2014/28591,2014,A2
[2]Patent: US2015/210687,2015,A1

11
[ 885520-23-0 ]
[ 1562194-72-2 ]

Reference： [1]Patent: WO2014/28591,2014,A2
[2]Patent: US2015/210687,2015,A1

12
[ 885520-23-0 ]
[ 1562194-75-5 ]

Reference： [1]Patent: WO2014/28591,2014,A2
[2]Patent: US2015/210687,2015,A1

13
[ 67-56-1 ]
[ 885520-23-0 ]
[ 201230-82-2 ]
[ 885521-44-8 ]

Yield	Reaction Conditions	Operation in experiment
48.3%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; at 70℃; under 2585.81 Torr; for 16h;	To a solution of 6-bromo-4-fluoro-lH-indazole (i-9c) (6.5 g, 0.03 mol) in 130 mL of methanol were added Pd(dppf)Cl2 (0.37 g, 0.005 mol) and triethylamine (6.15 g, 0.06 mol). Then the mixture was stirred at 70 C under 50 psi of CO for 16 h. The mixture was filtered and the filtrate was concentrated. The crude residue was purified by column chromatography on silica gel eluted with (PE / EtOAc = 5 : 1) to afford the title compound (2.8 g, yield: 48.3%) as a pale yellow solid. LCMS (ESI) calc'd for C9H7FN202 [M+H]+: 195, found: 195.
48.3%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; at 70℃; under 2585.81 Torr; for 16h;	iii). Preparation of methyl 4-fluoro-1H-indazole-6-carboxylate (i-9d) To a solution of <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong> (i-9c) (6.5 g, 0.03 mol) in 130 mL of methanol were added Pd(dppf)Cl2 (0.37 g, 0.005 mol) and triethylamine (6.15 g, 0.06 mol). Then the mixture was stirred at 70 C. under 50 psi of CO for 16 h. The mixture was filtered and the filtrate was concentrated. The crude residue was purified by column chromatography on silica gel eluted with (PE/EtOAc=5:1) to afford the title compound (2.8 g, yield: 48.3%) as a pale yellow solid. LCMS (ESI) calc'd for C9H7FN2O2 [M+H]+: 195. found: 195.

Reference： [1]Patent: WO2014/28591,2014,A2 .Location in patent: Page/Page column 51
[2]Patent: US2015/210687,2015,A1 .Location in patent: Paragraph 0264

14
[ 537013-51-7 ]
[ 885520-23-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrazine hydrate; In ethylene glycol; at 95℃; for 2h;Inert atmosphere;	To a stirred suspension of <strong>[537013-51-7]4-bromo-2,6-difluorobenzaldehyde</strong> 20 (commercially available, CAS 537013-51-7, 442.0 mg, 2.00 mmol) in ethylene glycol (10 mL) at ambient temperature was added hydrazine monohydrate (0.19 mL, 4.00 mmol). The resulting suspension was heated to 95 C under nitrogen for 2 h.The reaction was then cooled to 5 C and diluted with water. The solution was extracted with ethyl acetate, dried over anhydrous Na2SO4, and concentrated to yield 6-bromo-4-fluoro-1H-indazole 21 (430.0 mg, 100%) as a yellow solid.
74%	With hydrazine hydrate; In 1,4-dioxane; at 80℃; for 5h;	<strong>[537013-51-7]4-Bromo-2,6-difluorobenzaldehyde</strong> (2, 11.1 g, 50 mmoI) was dissolved in 1,4-dioxane (250 mL) and added with 80% hydrazine hydrate (31.3). g, 500 mmol), react at room temperature overnight, after TLC monitoring the reaction of the starting material, the reaction was heated to 80 C for 5 hours, the reaction solvent was spin-dried, 200 mL of ethyl acetate was dissolved, washed three times with water (50 mL×3), and the organic phase was used. Drying with sodium sulfate, concentrating by filtration and chromatography on silica gel (eluent: methylene chloride/methanol=200: 1-100:1) to give a yellow solid 3 (8.0 g, 74%)
71%	With hydrazine hydrate; In 1,4-dioxane; at 95℃; for 1.5h;	A mixture of <strong>[537013-51-7]4-bromo-2,6-difluorobenzaldehyde</strong> (50 g, 226 mmol) and N2H4-H2O (100 mL) in 1,4-dioxane (100 mL) was heated to 95 C. and stirred at this temperature for 1.5 h. After being cooled to r.t., the reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was dried and concentrated to give 6-bromo-4-fluoro-1H-indazole (35 g, 163 mmol, 71%) as a yellow solid, which was used for the next step without any further purification.

71%

With hydrazine hydrate; In 1,4-dioxane; at 95℃; for 1.5h;

At room temperature, 160 hydrazine hydrate (10 mL) was added into the solution of 161 <strong>[537013-51-7]4-bromo-2,6-difluorobenzaldehyde</strong> (5.00 g, 22.60 mmol) in 113 1,4-dioxane (10 mL), and the reaction was reacted at 95 C. for 1.5 hrs. After cooling to room temperature, it was added into the mixture of ice and water, extracted with ethyl acetate (50 mL×3), the organic layer was combined, dried over anhydrous sodium sulfate, and concentrated with pressure to afford 3.5 g of a yellow solid, yield was 71.0%. LC-MS(APCI): m/z=215.1 (M+1)

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 6194 - 6205
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 3187 - 3197
[3]Patent: CN110156754,2019,A .Location in patent: Paragraph 0020-0021; 0024-0025
[4]Patent: US2015/99782,2015,A1 .Location in patent: Paragraph 0225; 0226
[5]Patent: US2019/152954,2019,A1 .Location in patent: Paragraph 0354; 0355

15
[ 885520-23-0 ]
(R)-3-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-3-methylpiperidin-2-one [ No CAS ]

Reference： [1]Patent: US2015/99782,2015,A1

16
[ 885520-23-0 ]
[ 75-03-6 ]
6-bromo-1-ethyl-4-fluoro-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 1.25h;	Into a 25 ml round-bottom flask were placed a solution of <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong> (500 mg, 2.325 mmol, 1 equiv.) in DMF. Potassium carbonate (355 mg, 2.569 mmol, 1.1 equiv.), and iodoethane (474 mg, 3.039 mmol, 1.5 equiv.) were added. The reaction mixture was stirred for 15 min, and then the mixture was stirred for 1 h at 70 C. The reaction was monitored by LCMS. The mixture was concentrated under vacuum. The residue was purified by chromatogram on silica gel with ethyl acetate/petroleum ether (1:6) to yield 6-bromo-1-ethyl-4-fluoro-1H-indazole as brown oil and 210 mg 6-bromo-2-ethyl-4-fluoro-2H-indazole as brown solid.
	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 1.25h;	Into a 25 ml round-bottom flask were placed a solution of <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong> (500 mg, 2.325 mmol, 1 equiv.) in DMF. Potassium carbonate (355 mg, 2.569 mmol, 1.1 equiv.), and iodoethane (474 mg, 3.039 mmol, 1.5 equiv.) were added. The reaction mixture was stirred for 15 min, and then the mixture was stirred for 1 h at 70 C. The reaction was monitored by LCMS. The mixture was concentrated under vacuum. The residue was purified by chromatogram on silica gel with ethyl acetate/petroleum ether (1:6) to yield 6-bromo-1-ethyl-4-fluoro-1H-indazole as brown oil and 210 mg 6-bromo-2-ethyl-4-fluoro-2H-indazole as brown solid.

Reference： [1]Patent: US2019/47960,2019,A1 .Location in patent: Paragraph 0494; 0501; 0502
[2]Patent: US2019/47959,2019,A1 .Location in patent: Paragraph 0502-0503

17
[ 885520-23-0 ]
(R)-6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-3-(3-methyl-2-oxopiperidin-3-yl)pyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: US2015/99782,2015,A1

18
[ 885520-23-0 ]
[ 75-03-6 ]
6-bromo-1-ethyl-4-fluoro-1H-indazole [ No CAS ]
6-bromo-2-ethyl-4-fluoro-2H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%; 17%	With potassium carbonate; In dimethyl sulfoxide; at 18 - 25℃; for 16h;	To a solution of <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong> (1000 g, 4.65 mol) in DMSO (5.0 L), was added K2CO3 (900 g, 6.51 mol), followed by addition of ethyl iodide (900 g, 5.77 mol). The reaction mixture was stirred at r.t. for 16 h. The reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography (0-10% EtOAc in hexanes) to give 6-bromo-1-ethyl-4-fluoro-1H-indazole (595 g, 2.45 mol, 52%) as a yellow oil and 6-bromo-2-ethyl-4-fluoro-2H-indazole (278 g, 1.14 mol, yield 17%) as an orange solid. 1H NMR (600 MHz, CDCl3) delta 1.52 (t, 3H), 4.39 (q, 2H), 6.95 (dd, 1H), 7.40 (s, 1H), 8.02 (s, 1H). MS (ES+)(M+H) 243.
45%; 30%	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 5h;	To commercially available, <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong>,3 (35.0 g, 160 mmol) and K2CO3 (67.5 g, 488 mmol) in DMF (180 mL) was added ethyl iodide (76.2 g, 488 mmol) and stirred for 5 h at 50 C. The reaction was then dilutedwith water and extracted with ethyl acetate.The combined organic layers were dried over sodium sulfate andconcentrated. The crude product was purifiedby silica gel column chromatography (Petroleum ether : EtOAc 30:1) to provide 6-bromo-1-ethyl-4-fluoro-1H-indazole (4) (18 g, 45%) as a yellow oil and minor alkylation adduct 6-bromo-2-ethyl-4-fluoro-2H-indazole (4a) (12 g, 30%) as a yellow solid. (4) 1H NMR (400 MHz, CDCl3) delta: 8.01 (s, 1H); 7.38 (s, 1H); 6.79-7.04 (m, 1H); 4.38 (q, J = 7.60 Hz, 2H); 1.51 (t, J = 7.20 Hz, 3H).(4a) 1H NMR (400 MHz, CDCl3)delta: 7.98 (s, 1H); 7.67 (s, 1H); 6.84 (d, J= 9.54 Hz, 1H); 4.46 (q, J = 7.60 Hz,2H); 1.64 (t, J = 7.20 Hz, 3H).
210 mg	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 1.25h;	Into a 25 ml round-bottom flask were placed a solution of <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong> (500 mg, 2.325 mmol, 1 equiv.) in DMF. Potassium carbonate (355 mg, 2.569 mmol, 1.1 equiv.), and iodoethane (474 mg, 3.039 mmol, 1.5 equiv.) were added. The reaction mixture was stirred for 15 min, and then the mixture was stirred for 1 h at 70 C. The reaction was monitored by LCMS. The mixture was concentrated under vacuum. The residue was purified by chromatogram on silica gel with ethyl acetate/petroleum ether (1:6) to yield 6-bromo-1-ethyl-4-fluoro-1H-indazole as brown oil and 210 mg 6-bromo-2-ethyl-4-fluoro-2H-indazole as brown solid.

Reference： [1]Patent: US2015/99782,2015,A1 .Location in patent: Paragraph 0227
[2]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2670 - 2675
[3]Patent: US2019/47961,2019,A1 .Location in patent: Paragraph 0498-0499

19
[ 885520-23-0 ]
6-bromo-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)pyridin-2-yl]-4-fluoro-1H-indazole [ No CAS ]

Reference： [1]Patent: WO2016/11390,2016,A1

20
[ 885520-23-0 ]
C₃₁H₄₂FN₅O₂SSi [ No CAS ]

Reference： [1]Patent: WO2016/11390,2016,A1

21
[ 885520-23-0 ]
(S)-(6-(6-(6-(1-aminopropyl)pyridin-2-yl)-4-fluoro-1H-indazol-1-yl)pyridin-2-yl)methanol [ No CAS ]

Reference： [1]Patent: WO2016/11390,2016,A1

22
[ 885520-23-0 ]
C₂₅H₃₅BFN₃O₃Si [ No CAS ]

Reference： [1]Patent: WO2016/11390,2016,A1

23
[ 885520-23-0 ]
[ 33674-96-3 ]
[6-(6-bromo-4-fluoroindazol-1-yl)-pyridin-2-yl]methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With potassium phosphate; copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; In toluene; at 110℃; for 1h;Inert atmosphere;	6-Bromo-4-fluoro-lH-indazole (CAS No. 885520-23-0; 2.00 g, 9.30 mmol), 2-bromo-6- (hydroxylmethyl)pyridine (CAS No. 33674-96-3; 2.01 g, 10.7 mmol), K3P04 (3.95 g, 18.6 mmol) and copper(I) iodide (214 mg, 1.12 mmol) were charged to a flask and dried under vacuum for 10 minutes before flushing with nitrogen. Added toluene (38 mL) and trans- N,N'-dimethyl-cyclohexyl-l,2-diamine (350 uL, 2.2 mmol) before heating at 110 C for 1 h Filtered through Celite and washed with ethyl acetate. Concentrated and purified by flash chromatography (0-30% EtOAc:heptane). Collected 1.32 g of an off-white powder (44%). 1H NMR (400 MHz, CDCL3) delta 8.72 (s, 1H), 8.23 (s, 1H), 7.79 - 7.97 (m, 2H), 7.29 (s, 1H), 7.10 (d, J = 8.28 Hz, 1H), 4.91 (s, 2H).

Reference： [1]Patent: WO2016/11390,2016,A1 .Location in patent: Page/Page column 453; 454

24
[ 885520-23-0 ]
N-(5-(1-acetyl-4-methylpiperidin-4-yl)-1,3,4-thiadiazol-2-yl)-1-ethyl-4-fluoro-1H-indazole-6-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2670 - 2675

25
[ 885520-23-0 ]
N-(5-(1-acetyl-4-methylpiperidin-4-yl)-1,3,4-thiadiazol-2-yl)-1-ethyl-4-fluoro-1H-indazole-6-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2670 - 2675

26
[ 885520-23-0 ]
C₁₅H₁₄FN₅OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2670 - 2675

27
[ 885520-23-0 ]
methyl 1-ethyl-4-fluoro-1H-indazole-6-carboxylate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2670 - 2675

28
[ 885520-23-0 ]
1-ethyl-4-fluoro-N-(5-(4-methylpiperidin-4-yl)-1,3,4-thiadiazol-2-yl)-1H-indazole-6-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2670 - 2675

29
[ 885520-23-0 ]
1-ethyl-4-fluoro-1H-indazole-6-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2670 - 2675

30
[ 885520-23-0 ]
[ 74-88-4 ]
6-bromo-4-fluoro-1-methyl-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1 g		Intermediate B5: Synthesis of 6-bromo-4-fluoro-l-methyl-lH-indazole 6-Bromo-4-fluoro-lH-indazole (2.4 g, 11 mmol) is dissolved in THF (100 mL) and 60% sodium hydride (680 mg, 17 mmol) is added. After stirring for 10 min, methyl iodide (1.4 mL, 23 mmol) is added and the mixture is stirred for 16 hr. Then saturated NFLCl aqueous solution (25 mL) is added along with EtOAc (50 mL) and water (35 mL). The mixture is stirred for 5 min and the aqueous layer is separated and extracted with EtOAc (2x50 mL). All organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 1.0 g of the title product.

Reference： [1]Patent: WO2016/89800,2016,A1 .Location in patent: Page/Page column 57

31
[ 885520-23-0 ]
8-(4-fluoro-1-methyl-1H-indazol-6-yl)-3,4-dihydro-1H-pyrano[4,3-c]pyridin-4-ol [ No CAS ]

Reference： [1]Patent: WO2016/89800,2016,A1

32
[ 885520-23-0 ]
C₁₄H₁₈BFN₂O₂ [ No CAS ]

Reference： [1]Patent: WO2016/89800,2016,A1

33
[ 885520-23-0 ]
t-butyl 6-bromo-4-((4-(methoxycarbonyl)benzyl)oxy)-1H-indazole-1-carboxylate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 6194 - 6205

34
[ 885520-23-0 ]
t-butyl 6-bromo-4-((3-(methoxycarbonyl)benzyl)oxy)-1H-indazole-1-carboxylate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 6194 - 6205

35
[ 885520-23-0 ]
methyl 4-(((6-bromo-1H-indazol-4-yl)oxy)methyl)benzoate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 6194 - 6205

36
[ 885520-23-0 ]
methyl 3-(((6-bromo-1H-indazol-4-yl)oxy)methyl)benzoate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 6194 - 6205

37
[ 885520-23-0 ]
4-(((6-bromo-1H-indazol-4-yl)oxy)methyl)benzoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 6194 - 6205

38
[ 885520-23-0 ]
3-(((6-bromo-1H-indazol-4-yl)oxy)methyl)benzoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 6194 - 6205

39
[ 885520-23-0 ]
[ 24424-99-5 ]
t-butyl 6-bromo-4-fluoro-1H-indazole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With dmap; In dichloromethane; at 20℃; for 2h;Inert atmosphere;	To a solution of <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong> 21 (430.0 mg, 2.00 mmol) and DMAP (12.2 mg, 0.10 mmol) in DCM (10 mL) was added (Boc)2O (872.0 mg, 4.00 mmol). The mixture was stirred at ambient temperature for 2 h until the starting materiel was disappeared, then concentrated. The residue produced was purified through the column chromatography on silica gel with petroleum ether and ethyl acetate (60:1) as eluent to afford 22 (0.32 g, 50%) as colorless oil.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 6194 - 6205

40
[ 109-04-6 ]
[ 885520-23-0 ]
6-bromo-4-fluoro-1-(pyridin-2-yl)-1H-indazole [ No CAS ]
C₁₂H₇BrFN₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 3187 - 3197

41
[ 109-04-6 ]
[ 885520-23-0 ]
3-(4-(4-fluoro-1-(pyridin-2-yl)-1H-indazol-6-yl)phenyl)propanoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 3187 - 3197

42
[ 885520-23-0 ]
4-fluoro-6-(6-methylpyrazin-2-yl)-1H-indazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4458 - 4473

43
[ 885520-23-0 ]
1-(6-(1,4-diazepan-1-yl)pyridin-2-yl)-4-fluoro-6-(6-methylpyrazin-2-yl)-1H-indazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4458 - 4473

44
[ 885520-23-0 ]
tert-butyl 4-(6-(4-fluoro-6-(6-methylpyrazin-2-yl)-1H-indazol-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4458 - 4473

45
[ 885520-23-0 ]
[ 73183-34-3 ]
4-fluoro-1H-indazol-6-ylboronic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4458 - 4473

46
[ 886761-86-0 ]
[ 885520-23-0 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4458 - 4473

47
[ 885520-23-0 ]
tert-butyl 4-(2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-3-methylbutyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

48
[ 885520-23-0 ]
1-ethyl-4-fluoro-6-(6-methoxy-5-(3-methyl-1-(piperazin-1-yl)butan-2-yl)pyridin-2-yl)-1H-indazole [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

49
[ 885520-23-0 ]
1-ethyl-4-fluoro-6-(6-methoxy-5-(3-methyl-1-(4-(methylsulfonyl)piperazin-1-yl)butan-2-yl)pyridin-2-yl)-1H-indazole [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

50
[ 885520-23-0 ]
9-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-2-azaspiro[5.5] undecan-1-one [ No CAS ]

Reference： [1]Patent: US2019/47959,2019,A1
[2]Patent: US2019/47961,2019,A1

51
[ 885520-23-0 ]
1-ethyl-4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

52
[ 885520-23-0 ]
2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-3-methylbutanal [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

53
[ 885520-23-0 ]
ethyl 2-cyclopentylidene-2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)acetate [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

54
[ 885520-23-0 ]
ethyl 2-cyclopentyl-2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)acetate [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

55
[ 885520-23-0 ]
4-fluoro-1-isopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47961,2019,A1
[3]Patent: CN110156754,2019,A

56
[ 885520-23-0 ]
ethyl 2-ethyl-2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)butanoate [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

57
[ 885520-23-0 ]
5-(2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-2-oxoethyl)-1-(4-methoxybenzyl)-pyrrolidin-2-one [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

58
[ 885520-23-0 ]
5-(2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-2-hydroxy-3-methylbutyl)-1-(4-methoxybenzyl)pyrrolidin-2-one [ No CAS ]

Reference： [1]Patent: US2019/47959,2019,A1
[2]Patent: US2019/47961,2019,A1
[3]Patent: US2019/47960,2019,A1

59
[ 885520-23-0 ]
2-ethyl-2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-oxo-1,2-dihydropyridin-3-yl)butanoic acid [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

60
[ 885520-23-0 ]
2-ethyl-2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-oxo-1,2-dihydropyridin-3-yl)butanehydrazide [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

61
[ 885520-23-0 ]
3-(3-(1,3,4-oxadiazol-2-yl)pentan-3-yl)-6-(1-ethyl-4-fluoro-1H-indazol-6-yl)pyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: US2019/47959,2019,A1
[2]Patent: US2019/47961,2019,A1
[3]Patent: US2019/47960,2019,A1

62
[ 885520-23-0 ]
6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-3-(3-(5-isopropyl-1,3,4-oxadiazol-2-yl)pentan-3-yl)pyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47959,2019,A1
[3]Patent: US2019/47961,2019,A1

63
[ 885520-23-0 ]
6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-3-(3-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)pentan-3-yl)pyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: US2019/47959,2019,A1
[2]Patent: US2019/47961,2019,A1
[3]Patent: US2019/47960,2019,A1

64
[ 75-30-9 ]
[ 885520-23-0 ]
6-bromo-4-fluoro-1-isopropyl-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 6h;	4-Fluoro-6-bromo-1H-carbazole (3, 2.2 g, 10 mmol), potassium carbonate (1.7 g, 12 mmol) was dissolved in DMF (100 mL). 4, 2.6 g, 15 mmol), heated to 50 C for 6 hours. The reaction solution was poured into 200 mL of water, and the combined organic phase was combined with ethyl acetate, dried over anhydrous sodium sulfate, and filtered and concentrated on silica gel column (eluent: petroleum ether / ethyl acetate = 100:1 - 50:1) White solid 5a (2.1 g, 81%),
50.2%	With potassium carbonate; In dimethyl sulfoxide; at 20℃;	At room temperature, 164 2-iodopropane (1.58 g, 9.30 mmol) was added dropwise to 159 <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong> (1.60 g, 7.44 mmol) and 56 potassium carbonate (1.50 g, 11.16 mmol) in anhydrous 29 DMSO (8 mL), and the reaction was reacted at room temperature overnight. The reaction was quenched by adding 48 water, extracted with ethyl acetate (50 mL×3), the combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the filtrate was separated on column chromatography (eluant:petroleum ether/ethyl acetate (v/v)=9:1) to afford 960 mg of a pale yellow solid, yield was 50.2%. LC-MS(APCI): m/z=257.0 (M-1).
	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 80℃;	Into a 25-mL round-bottom flask, were placed a solution of <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong> (50 mg, 0.233 mmol, 1.00 equiv.) and potassium carbonate (44.993 mg, 0.326 mmol, 1.40 equiv.) in DMF (5 ml), then 2-iodopropane (51.388 mg, 0.302 mmol, 1.30 equiv.) was added. The resulting solution was stirred for 15 minutes at room temperature then stirred overnight at 80 C. The reaction was monitored by LCMS. The mixture was extracted with EtOAc, and the combined organic layer. The organic layer was evaporated under reduced pressure. The residue was purified by column chromatography (PE:EA=3:1) to yield 6-bromo-4-fluoro-1-isopropyl-1H-indazole as a yellow oil. Mass spectrum (EI, m/z): Calculated For C10H10BrFN2, 257.0 [M+H]+, found 258.9.

	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	Into a 25-mL round-bottom flask, were placed a solution of <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong> (50 mg, 0.233 mmol, 1.00 equiv.) and potassium carbonate (44.993 mg, 0.326 mmol, 1.40 equiv.) in DMF (5 ml), then 2-iodopropane (51.388 mg, 0.302 mmol, 1.30 equiv.) was added. The resulting solution was stirred for 15 minutes at room temperature then stirred overnight at 80 C. The reaction was monitored by LCMS. The mixture was extracted with EtOAc, and the combined organic layer. The organic layer was evaporated under reduced pressure. The residue was purified by column chromatography (PE:EA=3:1) to yield 6-bromo-4-fluoro-1-isopropyl-1H-indazole as a yellow oil. Mass spectrum (EI, m/z): Calculated For C10H10BrFN2, 257.0 [M+H]+, found 258.9.
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	Into a 25-mL round-bottom flask, were placed a solution of <strong>[885520-23-0]6-bromo-4-fluoro-1H-indazole</strong> (50 mg, 0.233 mmol, 1.00 equiv.) and potassium carbonate (44.993 mg, 0.326 mmol, 1.40 equiv.) in DMF (5 ml), then 2-iodopropane (51.388 mg, 0.302 mmol, 1.30 equiv.) was added. The resulting solution was stirred for 15 minutes at room temperature then stirred overnight at 80 C. The reaction was monitored by LCMS. The mixture was extracted with EtOAc, and the combined organic layer. The organic layer was evaporated under reduced pressure. The residue was purified by column chromatography (PE:EA=3:1) to yield 6-bromo-4-fluoro-1-isopropyl-1H-indazole as a yellow oil. Mass spectrum (EI, m/z): Calculated For C10H10BrFN2, 257.0 [M+H]+, found 258.9.

Reference： [1]Patent: CN110156754,2019,A .Location in patent: Paragraph 0020-0021; 0026-0027
[2]Patent: US2019/152954,2019,A1 .Location in patent: Paragraph 0354; 0356
[3]Patent: US2019/47960,2019,A1 .Location in patent: Paragraph 0601; 0602; 0603
[4]Patent: US2019/47959,2019,A1 .Location in patent: Paragraph 0601-0602
[5]Patent: US2019/47961,2019,A1 .Location in patent: Paragraph 0600-0601

65
[ 885520-23-0 ]
C₂₁H₂₈BrN₃O₃S [ No CAS ]