[ CAS No. 552331-30-3 ] {[proInfo.proName]}

Name: 552331-30-3|5-Bromo-1,3-dimethyl-1H-indazole|98%
Brand: Ambeed
SKU: A133580
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Quality Control of [ 552331-30-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 552331-30-3 ]

SDS Specification

Alternatived Products of [ 552331-30-3 ]

Product Details of [ 552331-30-3 ]

CAS No. :	552331-30-3	MDL No. :	MFCD12028623
Formula :	C₉H₉BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FMYUTSXDZFFESE-UHFFFAOYSA-N
M.W :	225.09	Pubchem ID :	22607588
Synonyms :

Calculated chemistry of [ 552331-30-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.66
TPSA :	17.82 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) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.23
Log Po/w (XLOGP3) :	2.66
Log Po/w (WLOGP) :	2.64
Log Po/w (MLOGP) :	2.49
Log Po/w (SILICOS-IT) :	2.54
Consensus Log Po/w :	2.51

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.47
Solubility :	0.0769 mg/ml ; 0.000342 mol/l
Class :	Soluble
Log S (Ali) :	-2.69
Solubility :	0.464 mg/ml ; 0.00206 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.72
Solubility :	0.0429 mg/ml ; 0.000191 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 552331-30-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 552331-30-3 ]

* 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 [ 552331-30-3 ]
Downstream synthetic route of [ 552331-30-3 ]

[ 552331-30-3 ] Synthesis Path-Upstream 1~6

1
[ 552331-16-5 ]
[ 74-88-4 ]
[ 552331-30-3 ]

Yield	Reaction Conditions	Operation in experiment
67%	With NaH In N,N-dimethyl-formamide	Example 112A 5-Bromo-1,3-dimethyl-1H-indazole Example 102C (500 mg; 2.37 mmol) was added to a mixture of 60percent NaH (115 mg; 2.84 mmol) in DMF (10 mL). After 15 min. at r.t. iodomethane (456 mg; 3.21 mmol) was added, the reaction was stirred for 2 hrs then diluted with water and extracted with EtOAc. The extracts were rinsed with water and brine, dried (MgSO₄), evaporated, and isolated by flash chromatography (1:1 Et₂O:hexane) to give the desired product (360 mg; 67percent).
67%	Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25 h; Stage #2: at 20℃; for 2 h;	Example 112A 5-Bromo-1,3-dimethyl-1H-indazole Example 102C (500 mg; 2.37 mmol) was added to a mixture of 60percent NaH (115 mg; 2.84 mmol) in DMF (10 mL). After 15 min. at r.t. iodomethane (456 mg; 3.21 mmol) was added, the reaction was stirred for 2 hrs then diluted with water and extracted with EtOAc. The extracts were rinsed with water and brine, dried (MgSO₄), evaporated, and isolated by flash chromatography (1:1 Et₂O:hexane) to give the desired product (360 mg; 67percent).
67%	With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.25 h; Inert atmosphere	To a stirred solution of 5-bromo-3-methyl- 1H-indazole (2.51 g, 11.6 mmol), dissolved in N,N-dimethylformamide (30 mL) and cooled to 0°C under nitrogen, was added portionwise sodium hydride (60percent dispersion in mineral oil; 596 mg, 14.9 mmol).The dark brown, effervescing solution was stirred for 70 minutes prior to addition of iodomethane (0.87 mL, 14 mmol). The reaction mixture was stirred at 0°C for 15 minutes before warming to r.t. A brown-orange solid was formed and the mixture was stirred for 3 h prior to the addition of water (30 mL) and EtOAc (30 mL). The mixture was stirred for 40 minutes before leaving to stand overnight. Further EtOAc (20 mL) andwater (20 mL) were added, then the organic layer was separated. The aqueous layer was re-extracted with further EtOAc (2 x 50 mL). The organic layers were combined, dried with anhydrous sodium sulfate and filtered under reduced pressure, then the solvent was removed in vacuo. The resulting brown oil was purified by flash column chromatography on silica (gradient elution with 0-100percent EtOAc/isohexane) to afford the title compound (1.75 g, 67percent) as an orange oil. oH (DMSO-d6, 300 MHz) 7.94 (dd, J 1.7, 0.7 Hz, 1H), 7.55 (dd,J8.8, 0.7 Hz, 1H), 7.46 (dd,J8.9, 1.8 Hz, 1H), 3.95 (s, 3H), 2.45 (s, 3H). LCMS (ES+) [M+H] 227.0, RT 2.00 minutes (method 3).

39%

Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5 h;
Stage #2: at 0℃; for 4 h;

To a stirred suspension of NaH (60percent oil dispersion, 136 mg,2.83 mmol) in DMF (10 mL) was added a solution of 24 (400 mg,1.89 mmol) in DMF (2 mL) at 0 C, and the mixture was stirred atthe same temperature for 30 min. MeI (400 lL, 2.83 mmol) wasadded and the resulting mixture was stirred at 0 C for 4 h. Thereaction mixture was quenched with water and extracted withEtOAc. The combined EtOAc layers were washed with brine, driedover Na2SO4, and concentrated. The residue was purified by columnchromatography (silica gel, hexane/EtOAc = 80/20) to givethe title compound (200 mg, 39percent) as a yellow oil. 1H NMR(400 MHz, DMSO-d6) d 2.45 (3H, s), 3.95 (3H, s), 7.46 (1H, dd,J = 8.9, 1.8 Hz), 7.54 (1H, d, J = 8.9 Hz), 7.94 (1H, d, J = 1.5 Hz). MS(ESI/APCI) m/z = 225.0 [M+H]+.

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 20, p. 6832 - 6846
[2] Patent: US2003/187026, 2003, A1,
[3] Patent: US2003/199511, 2003, A1, . Location in patent: Page/Page column 41
[4] Patent: WO2017/55305, 2017, A1, . Location in patent: Page/Page column 53
[5] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 11, p. 2504 - 2518

2
[ 552331-16-5 ]
[ 74-88-4 ]
[ 552331-30-3 ]

Reference： [1] Patent: WO2015/42397, 2015, A1, . Location in patent: Paragraph 0001131

3
[ 552331-16-5 ]
[ 4637-24-5 ]
[ 552331-30-3 ]

Reference： [1] Synlett, 2013, vol. 24, # 5, p. 570 - 574

4
[ 552331-15-4 ]
[ 552331-30-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 20, p. 6832 - 6846

5
[ 198477-89-3 ]
[ 552331-30-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 20, p. 6832 - 6846

6
[ 93777-26-5 ]
[ 552331-30-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 20, p. 6832 - 6846

[ 552331-30-3 ] Synthesis Path-Downstream 1~39

1
[ 900517-08-0 ]
[ 552331-30-3 ]
[ 911305-65-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6832 - 6846

2
[ 552331-16-5 ]
[ 74-88-4 ]
[ 552331-30-3 ]

Yield	Reaction Conditions	Operation in experiment
67%	With NaH; In N,N-dimethyl-formamide;	Example 112A 5-Bromo-1,3-dimethyl-1H-indazole Example 102C (500 mg; 2.37 mmol) was added to a mixture of 60% NaH (115 mg; 2.84 mmol) in DMF (10 mL). After 15 min. at r.t. iodomethane (456 mg; 3.21 mmol) was added, the reaction was stirred for 2 hrs then diluted with water and extracted with EtOAc. The extracts were rinsed with water and brine, dried (MgSO4), evaporated, and isolated by flash chromatography (1:1 Et2O:hexane) to give the desired product (360 mg; 67%).
67%		Example 112A 5-Bromo-1,3-dimethyl-1H-indazole Example 102C (500 mg; 2.37 mmol) was added to a mixture of 60% NaH (115 mg; 2.84 mmol) in DMF (10 mL). After 15 min. at r.t. iodomethane (456 mg; 3.21 mmol) was added, the reaction was stirred for 2 hrs then diluted with water and extracted with EtOAc. The extracts were rinsed with water and brine, dried (MgSO4), evaporated, and isolated by flash chromatography (1:1 Et2O:hexane) to give the desired product (360 mg; 67%).
67%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20℃; for 0.25h;Inert atmosphere;	To a stirred solution of 5-bromo-3-methyl- 1H-indazole (2.51 g, 11.6 mmol), dissolved in N,N-dimethylformamide (30 mL) and cooled to 0C under nitrogen, was added portionwise sodium hydride (60% dispersion in mineral oil; 596 mg, 14.9 mmol).The dark brown, effervescing solution was stirred for 70 minutes prior to addition of iodomethane (0.87 mL, 14 mmol). The reaction mixture was stirred at 0C for 15 minutes before warming to r.t. A brown-orange solid was formed and the mixture was stirred for 3 h prior to the addition of water (30 mL) and EtOAc (30 mL). The mixture was stirred for 40 minutes before leaving to stand overnight. Further EtOAc (20 mL) andwater (20 mL) were added, then the organic layer was separated. The aqueous layer was re-extracted with further EtOAc (2 x 50 mL). The organic layers were combined, dried with anhydrous sodium sulfate and filtered under reduced pressure, then the solvent was removed in vacuo. The resulting brown oil was purified by flash column chromatography on silica (gradient elution with 0-100% EtOAc/isohexane) to afford the title compound (1.75 g, 67%) as an orange oil. oH (DMSO-d6, 300 MHz) 7.94 (dd, J 1.7, 0.7 Hz, 1H), 7.55 (dd,J8.8, 0.7 Hz, 1H), 7.46 (dd,J8.9, 1.8 Hz, 1H), 3.95 (s, 3H), 2.45 (s, 3H). LCMS (ES+) [M+H] 227.0, RT 2.00 minutes (method 3).

39%

To a stirred suspension of NaH (60% oil dispersion, 136 mg,2.83 mmol) in DMF (10 mL) was added a solution of 24 (400 mg,1.89 mmol) in DMF (2 mL) at 0 C, and the mixture was stirred atthe same temperature for 30 min. MeI (400 lL, 2.83 mmol) wasadded and the resulting mixture was stirred at 0 C for 4 h. Thereaction mixture was quenched with water and extracted withEtOAc. The combined EtOAc layers were washed with brine, driedover Na2SO4, and concentrated. The residue was purified by columnchromatography (silica gel, hexane/EtOAc = 80/20) to givethe title compound (200 mg, 39%) as a yellow oil. 1H NMR(400 MHz, DMSO-d6) d 2.45 (3H, s), 3.95 (3H, s), 7.46 (1H, dd,J = 8.9, 1.8 Hz), 7.54 (1H, d, J = 8.9 Hz), 7.94 (1H, d, J = 1.5 Hz). MS(ESI/APCI) m/z = 225.0 [M+H]+.

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6832 - 6846
[2]Patent: US2003/187026,2003,A1
[3]Patent: US2003/199511,2003,A1 .Location in patent: Page/Page column 41
[4]Patent: WO2017/55305,2017,A1 .Location in patent: Page/Page column 53
[5]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 2504 - 2518

3
[ 552331-15-4 ]
[ 552331-30-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6832 - 6846

4
[ 198477-89-3 ]
[ 552331-30-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6832 - 6846

5
[ 552331-30-3 ]
(S)-1-[(1H-indol-3-yl)methyl]-2-[5-(3-methyl-1H-indazol-5-yl)pyridin-3-yl]oxy}ethylamine trifluoroacetic acid salt [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6832 - 6846

6
[ 93777-26-5 ]
[ 552331-30-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6832 - 6846

7
[ 552331-30-3 ]
[ 73183-34-3 ]
[ 1220696-53-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 80℃; for 16.3h;Inert atmosphere;	To a solution of Intermediate 18 (1.43 g, 6.35 mmol) in 1,4-dioxane (15 mL) wereadded bis(pinacolato)diboron (1.77 g, 6.99 mmol) and potassium acetate (1.25 g, 12.71mmol), then the system was degassed under nitrogen for 30 minutes. [1,1?-Bis(diphenyl- phosphino)ferrocene]dichloropalladium(II) complex with DCM (0.26 g, 0.32 mmol) was added and the mixture was heated at 80C for 16 h. Upon cooling to r.t., the reaction mixture was diluted with EtOAc and filtered through a pad of Celite which was washedwith additional EtOAc, then the combined filtrates were concentrated in vacuo. Theresidue was purified by flash column chromatography on silica (gradient elution with 0-100% EtOAc in heptane) to afford the title compound (1.61 g, 91%) as a white solid. 0H(DMSO-d6, 500 MHz) 8.09-8.01 (m, 1H), 7.62 (dd,J8.5, 0.9 Hz, 1H), 7.52 (dd,J8.5, 0.8Hz, 1H), 3.95 (s, 3H), 2.49 (s, 3H), 1.31 (s, 12H). LCMS (ES+) [M+H] 273, RT 1.25minutes (method 5).
80%	With potassium acetate; In 1,4-dioxane; at 100℃; for 3h;	To a stirred solution of <strong>[552331-30-3]<strong>[552331-30-3]5-bromo-1,3-dimethyl-1H-indazol</strong>e</strong> (5.4 g, 0.023 mol) and 4,4,5,5,4?,4?,5?,5?-octamethyl-[2,2?]bi[[1,3,2]dioxaborolanyl] (7.3 g. 0.0287 mol) in dioxane (54 mL, 10 V) were added potassium acetate (7.05 g, 0.0719 mol) and palladium tetrakis (1.38 g, 0.0011 mol) under room temperature. The resulting reaction mass was stirred at 100 C. over a period of 3 hours. The reaction was monitored by TLC. The reaction mass was diluted with ethyl acetate (200 mL) and filtered through a celite pad. The organic layer was washed with water (500 mL), brine (250 mL), dried over anhydrous sodium sulphate and concentrated. The crude product obtained was purified by silica gel (230-400) column chromatography (15% ethyl acetate in hexane) to obtain tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole as an off-white solid (5.2 g, 80%).
52.1%	With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In 1,4-dioxane; at 80 - 95℃; for 28h;Inert atmosphere;	To a solution of 5-bromo-l ,3 -dimethyl- 1 H-indazole (26 g, 1 15 mmol) and bispinacolato diboron (32.3 g, 127 mmol) in l,4-dioxan (260 mL) was added KOAc (34 g, 345 mmol ). The reaction was degassed with N2 for 10 min and then Pd(PPhd4 (6.6 g, 5.57 mmol) was added and heated at 95C for l6h. Upon completion of addition, the reaction was heated at 80C for l2h. Upon completion, the reaction was filtered through celite, the filtrate was concentrated. The obtained crude was purified by flash column chromatography (neutral alumina) eluting the required compound 1 ,3-dimcthyl-5-(4,4,5,5-tctramcthyl-[ l ,3,2]dioxaborolan-2-yl)- 1 //-indazolc (18 g, 52.1%) with 5% ethylacetate -hexanes as an off-white solid compound.

52.1%	With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In 1,4-dioxane; at 80 - 95℃; for 28h;Inert atmosphere;	To a solution of 5-bromo-l,3-dimethyl-lH-indazole (26 g, 115 mmol) and bispinacolato diboron (32.3 g, 127 mmol) in l,4-dioxan (260 mL) was added KOAc (34 g, 345 mmol ). The reaction was degassed with N2 for 10 min and then Pd(PPh3)4 (6.6 g, 5.57 mmol) was added and heated at 95C for l6h. Upon completion of addition, the reaction was heated at 80C for l2h. Upon completion, the reaction was filtered through celite, the filtrate was concentrated. The obtained crude product was purified by flash column chromatography (neutral alumina) eluting the required compound l,3-dimethyl-5-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)- lH-indazole (18 g, 52.1%) with 5% ethylacetate-hexanes as an off-white solid compound.
	With potassium acetate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; for 2h;Inert atmosphere; Reflux;	Intermediate 45: 4^1,3-dimethyI-lH-mdazol-5-yI)-2^ acetate (0.344 g, 3.51 mraol) and bis( macolato)diborori (351 mg, 1.4 mmol) were added to a solution of 5-bromo-l,3-dimethyl-lH-inda2X>le (240 mg, 1.06 mmol) in dioxane (10 ml) and mixture was degassed with nitrogen for 30 min. teiiakiUSD(-riphenylpbosphijie) paUadium(O) was added and degassed for further 30 min. Reaction mixture was refluxed for 2 h. After completion of the reaction, work-up (AcOEt/l¾0) followed by column afforded 1,3- aimethyl-5-(4,4,5,5-tetrame&yM^ (85 mg) as a white solid. The title compound (26 mg) was prepared from 4-bromo-2,6HMfluoroaniline (50 mg, 0,24 mmol) and l,3-dimemyl-5-(4,4,5,5-teta_me^(85 mg, 0.31 mmol) as a white solii ]H- M (5 ppm, DMSO-i¾, 400 MHz): 7.93 (s, 1H), 7.66 (dd, J 1.5, 8.8, lH), 7.55 (d, J 8.8, 1H), 7.33 (dd, J 2, 8.2, 2H), 5.22 (s, 2H), 3.94 (s, 3H), 2.49 (s, 3H).

Reference： [1]Patent: WO2017/55305,2017,A1 .Location in patent: Page/Page column 54
[2]Patent: US2020/31833,2020,A1 .Location in patent: Paragraph 0281; 0282
[3]Patent: WO2020/74159,2020,A1 .Location in patent: Page/Page column 23
[4]Patent: WO2020/74160,2020,A1 .Location in patent: Page/Page column 34; 38
[5]Patent: WO2011/138665,2011,A1 .Location in patent: Page/Page column 45

8
[ 552331-30-3 ]
[ 1095539-94-8 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 8827 - 8837,11

9
[ 552331-30-3 ]
[ 1095535-45-7 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 8827 - 8837,11

10
[ 552331-30-3 ]
[ 170033-47-3 ]
[ 1095539-92-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 8827 - 8837,11

11
[ 552331-16-5 ]
[ 4637-24-5 ]
5-bromo-2,3-dimethyl-2H-indazole [ No CAS ]
[ 552331-30-3 ]

Reference： [1]Synlett,2013,vol. 24,p. 570 - 574

12
[ 552331-16-5 ]
[ 74-88-4 ]
5-bromo-2,3-dimethyl-2H-indazole [ No CAS ]
[ 552331-30-3 ]

Yield	Reaction Conditions	Operation in experiment
		[0001131] To Compound 310A (1.9 g, 9.05 mmol) in DMF (15 mL) was added sodium hydride (60% in mineral, 398 mg, 9.96 mmol) with ice bath cooling. The mixture was stirred for 30 min at room temperature and iodomethane (0.94 mL, 27.15 mmol) was added. The reaction mixture was stirred at room temperature for 3 h, quenched with ammonium chloride solution (30 mL), and extracted with ethyl acetate (100 mL x 3). The combined organic layers were washed with brine (200 mL), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0%> to 90%> v/v) to give Compound 318A and Compound 318B.

Reference： [1]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 0001131

13
[ 552331-30-3 ]
N-((1R,2R)-1-(3-chloro-4-cyclopropoxyphenyl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)-2-(4-(1,3-dimethyl-1H-indazol-5-yl)phenyl)-2-oxoacetamide [ No CAS ]

Reference： [1]Patent: WO2015/42397,2015,A1

14
[ 552331-30-3 ]
2-(4-(1,3-dimethyl-1H-indazol-5-yl)phenyl)-N-((1R,2R)-1-(8-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)-2-oxoacetamide [ No CAS ]

Reference： [1]Patent: WO2015/42397,2015,A1

15
[ 552331-30-3 ]
ethyl 2-oxo-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate [ No CAS ]
C₁₇H₁₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 2h;	[0001132] A mixture of Compound 318B (225 mg, 1 mmol), Compound 175B (477 mg, 1.57 mmol), Pd(PPh3)2Cl2 (70 mg, 0.1 mmol), and K2C03 (256 mg, 2 mmol) in dioxane (5 mL) and water (0.5 mL) was stirred at 80 C for 2 h. The mixture was cooled down and filtered. The precipitate dissolved with water (10 mL) and purified with reverse phase chromatography using eluent (methanol in water, from 0% to 100% v/v) to yield Compound 318C.

Reference： [1]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 0001132

16
[ 552331-30-3 ]
[ 191090-84-3 ]
4-[(4-chlorobenzyl)oxy]-1-(1,3-dimethyl-1H-indazol-5-yl)pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With copper(l) iodide; (±)-N,N-dimethyl-trans-1,2-diaminocyclohexane; potassium carbonate; In 1,4-dioxane; at 110℃; for 16h;	To a mixture of 25 (200 mg, 0.88 mmol), 6a (168 mg,0.77 mmol), and K2CO3 (368 mg, 2.66 mmol) in dioxane (10 mL)were added CuI (51 mg, 0.36 mmol) and trans-N,N0-dimethylcyclohexane-1,2-diamine (68 mg, 0.36 mmol). The mixture washeated at 110 C for 16 h. The mixture was cooled to rt and concentrated.The residue was diluted with DCM, washed with brine,dried over Na2SO4, and concentrated. The residue was purified bycolumn chromatography (silica gel, DCM/MeOH = 97/3) to givethe title compound (100 mg, 34%) as a off-white solid; mp172-173 C. 1H NMR (400 MHz, DMSO-d6) d 2.47 (3H, s), 3.99(3H, s), 5.16 (2H, s), 5.97 (1H, d, J = 2.6 Hz), 6.10 (1H, dd, J = 7.6,2.6 Hz), 7.30 (1H, dd, J = 8.8, 1.7 Hz), 7.49 (4H, s), 7.60 (1H, d,J = 2.1 Hz), 7.62 (1H, d, J = 3.5 Hz), 7.68 (1H, d, J = 1.4 Hz). 13CNMR (101 MHz, DMSO-d6) d 11.4, 35.1, 68.7, 97.8, 99.9, 109.6,118.2, 122.4, 125.5, 128.5, 129.7, 132.7, 133.0, 134.9, 139.4,139.7, 140.6, 162.8, 166.7. MS (ESI/APCI) m/z = 380.0 [M+H]+. Anal.Calcd for C21H18ClN3O2: C, 66.40; H, 4.78; N, 11.06. Found:C, 66.35; H, 4.84; N, 11.09.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 2504 - 2518

17
[ 552331-30-3 ]
ethyl 4-[7-amino-3-(1,3-dimethyl-1H-indazol-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/55305,2017,A1

18
[ 552331-30-3 ]
ethyl 4-[7-(N-[(tert-butoxy)carbonyl]-N-[3-(methanesulfonyl)phenyl]methyl}amino)-3-(1,3-dimethyl-1H-indazol-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/55305,2017,A1

19
[ 552331-30-3 ]
ethyl 4-[7-(benzylamino)-3-(1,3-dimethyl-1H-indazol-5-yl)-2-methylpyrazolo[1,5-a]-pyrimidin-5-yl]piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/55305,2017,A1

20
[ 552331-30-3 ]
[ 557-21-1 ]
1,3-dimethyl-1H-indazole-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	To a stirred solution of 5-bromo-1 ,3-dimethyl-1 H-indazole (600 mg, 2.67 mmol) in N,Ndimethylformamide (10 mL) was added zinc cyanide (313 mg, 2.67 mmol, 169 iL) and tetrakis(triphenylphosphine)palladium(0) (308 mg, 267 imol) under nitrogen. The mixture was stirred at100 00 for 16 h, then cooled to 20 00, and diluted with water (15 mL). The reaction mixture was extracted with ethyl acetate (40 mL x 3). The combined organic phases were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give crude product. This was triturated with petroleum ether (30 mL) and dichloromethane (5 mL), filtered and the filter cake dried in vacuo to give 1 ,3-dimethyl-1 H-indazole-5-carbonitrile (340 mg, 1 .99mmol, 74%) as a brown solid. 1H NMR (400 MHz, ODd3) O 8.02 (s, 1H), 7.54 (d, J8.8 Hz, 1H), 7.37 (d, J8.8 Hz, 1 H), 4.02 (s, 3H), 2.57 (s, 3H).

Reference： [1]Patent: WO2018/81167,2018,A1 .Location in patent: Page/Page column 193

21
[ 552331-30-3 ]
N-(2-(4-(3-(1,3-dimethyl-1H-indazol-5-yl)-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-2-oxoethyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2018/81167,2018,A1

22
[ 552331-30-3 ]
(Z)-N’-hydroxy-1,3-dimethyl-1H-indazole-5-carboximidamide [ No CAS ]

Reference： [1]Patent: WO2018/81167,2018,A1

23
[ 552331-30-3 ]
C₁₈H₁₇Cl₂N₅O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2020,vol. 30

24
[ 552331-30-3 ]
C₁₉H₂₀ClN₅O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2020,vol. 30

25
[ 552331-30-3 ]
C₁₀H₁₀N₂O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2020,vol. 30

26
[ 552331-30-3 ]
[ 201230-82-2 ]
[ 68-12-2 ]
C₁₁H₁₂N₂O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2020,vol. 30

27
[ 198477-89-3 ]
[ 60-34-4 ]
[ 552331-30-3 ]

Yield	Reaction Conditions	Operation in experiment
52.4%	With pyridine; at 100℃; for 16h;	To a stirred solution of 1-(5-bromo-2-fluoro-phenyl)-ethanone (10.0 g, 0.046 mol) in pyridine (50 mL) was added methyl hydrazine (2.7 mL, 0.050 mol) at room temperature. The resulting reaction mass was stirred at 100 C. for 16 hours. The crude product obtained after complete evaporation of the volatiles was diluted with water (50 mL) and extracted with ethyl acetate (100 mL*2). The organic layers were combined, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the product as a pale yellow solid. The crude product was purified by silica gel (230-400) column chromatography (15% ethyl acetate in hexane) to obtain 5-bromo-1,3-dimethyl-1H-indazole as a pale yellow oil (5.4 g, 52.4%).
41.8%	With pyridine; at 90℃; for 10h;	A stirred solution of l-(5-bromo-2-fluorophenyl)ethanone (50 g, 230 mmol) and N-methyl hydrazine (42.4 mL, 805 mmol) in pyridine (500 mL) was heated at 90C for lOh. Upon completion, the pyridine in the reaction was distilled out. The crude was partitioned between water and ethylacetate. The ethylacetate layers were dried over sodium sulfate and concentrated. The obtained crude was purified by flash column chromatography (neutral alumina) eluting the required compound 5-bromo-l ,3 -dimethyl- 1 H-indazole (20.23 g, 41.8%) with 2% ethylacetate - hexanes as a pale brown viscous compound.
41.8%	In pyridine; at 90℃; for 10h;	A stirred solution of l-(5-bromo-2-fluorophenyl)ethanone (50 g, 230 mmol) and N-methyl hydrazine (42.4 mL, 805 mmol) in pyridine (500 mL) was heated at 90C for lOh. Upon completion, the pyridine in the reaction was distilled out. The crude product was partitioned between water and ethylacetate. The ethylacetate layers were dried over sodium sulfate and concentrated. The obtained crude product was purified by flash column chromatography (0155) (neutral alumina) eluting the required compound 5-bromo-l,3-dimethyl-lH-indazole (20.23 g, 41.8%) with 2% ethylacetate-hexanes as a pale brown viscous compound.

Reference： [1]Patent: US2020/31833,2020,A1 .Location in patent: Paragraph 0279; 0280
[2]Patent: WO2020/74159,2020,A1 .Location in patent: Page/Page column 23
[3]Patent: WO2020/74160,2020,A1 .Location in patent: Page/Page column 34; 38

28
[ 552331-30-3 ]
3-(1,3-dimethyl-1H-indazol-5-yl)-2,6-dimethyl-N-(pyridin-4-ylmethyl)imidazo[1,2-b]pyridazin-8-amine [ No CAS ]

Reference： [1]Patent: US2020/31833,2020,A1
[2]Patent: WO2020/74160,2020,A1

29
[ 552331-30-3 ]
3-(1,3-dimethyl-1H-indazol-5-yl)-2,5-dimethyl-N-[(pyridin-4-yl)methyl]pyrazolo[1,5-a]pyrimidin-7-amine [ No CAS ]

Reference： [1]Patent: US2020/31833,2020,A1
[2]Patent: WO2020/74160,2020,A1

30
[ 552331-30-3 ]
8-(1,3-dimethyl-1H-indazol-5-yl)-2,7-dimethyl-N-(pyridin-4-ylmethyl)pyrazolo[1,5-a][1,3,5]triazin-4-amine [ No CAS ]

Reference： [1]Patent: US2020/31833,2020,A1
[2]Patent: WO2020/74160,2020,A1

31
[ 552331-16-5 ]
[ 74-88-4 ]
[ 552331-30-3 ]
5-bromo-2,3-dimethyl-1H-indazol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%; 27%		To a suspension of sodium hydride (0.98 g, 24.5 mmol, 60 % in mineral oil) in A^/V-dimethylformamide (70 mL), 5-bromo-3-methyl-li7-indazol (4.30 g, 20.4 mmol) was added in portions under an inert atmosphere at room temperature, and the obtained suspension was stirred further for 15 minutes lodomethane (1.7 ml, 27.5 mmol) was added, and the mixture was stirred further for 3 hours at room temperature. Water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with 2 M Na2S203 solution and water, dried over Na2S04, and evaporated to dryness. The regioisomeric products w?ere separated by column chromathography on silica gel, using a mixture of ethyl acetate and cyclohexane (2: 1) as eluent. Yield: 3 16 g (69 %) for the desired product 5-bromo-l,3- dimethyl- l//-indazoi and 1.26 g (27 %) for 5-bromo-2,3-dimethyl-l//-indazol

Reference： [1]Patent: WO2020/12423,2020,A1 .Location in patent: Page/Page column 35; 41

32
[ 552331-30-3 ]
1-chloroethyl (3-(1,3-dimethyl-1H-indazol-5-yl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl)(pyridin-4-ylmethyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2020/74160,2020,A1

33
[ 552331-30-3 ]
1-[(3-(1,3-dimethyl-1H-indazol-5-yl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl)(pyridin-4-ylmethyl)carbamoyl]oxy}ethyl acetate [ No CAS ]

Reference： [1]Patent: WO2020/74160,2020,A1

34
[ 552331-30-3 ]
[3-(1,3-dimethyl-1H-indazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-pyridin-4-ylmethylcarbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: WO2020/74160,2020,A1

35
[ 552331-30-3 ]
[3-(1,3-dimethyl-1H-indazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]pyridin-4-ylmethylamine [ No CAS ]

Reference： [1]Patent: WO2020/74160,2020,A1

36
[ 552331-30-3 ]
[3-(1,3-dimethyl-1H-indazol-5-yl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl](2-fluoropyridin-4-ylmethyl)carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: WO2020/74159,2020,A1

37
[ 552331-30-3 ]
3-(1,3-dimethyl-1H-indazol-5-yl)-2,5-dimethyl-N-[(2-fluoropyridin-4-yl)methyl]pyrazolo[1,5-a]pyrimidin-7- amine [ No CAS ]

Reference： [1]Patent: WO2020/74159,2020,A1

38
[ 552331-30-3 ]
[3-(1,3-dimethyl-1H-indazol-5-yl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl](2-methylpyridin-4-ylmethyl)carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: WO2020/74159,2020,A1

39
[ 552331-30-3 ]
3-(1,3-dimethyl-1H-indazol-5-yl)-2,5-dimethyl-N-[(2-methylpyridin-4-yl)methyl]pyrazolo[1,5-a]pyrimidin-7- amine [ No CAS ]

Reference： [1]Patent: WO2020/74159,2020,A1

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[ 552331-30-3 ]

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Ghs Precautionary Statements

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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
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P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
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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) ]}	Inquiry {[ 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. 552331-30-3 ] {[proInfo.proName]}

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[ 552331-30-3 ] Synthesis Path-Upstream 1~6

[ 552331-30-3 ] Synthesis Path-Downstream 1~39

Related Functional Groups of [ 552331-30-3 ]

Bromides

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Indazoles

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[ 552331-30-3 ]

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[ 552331-30-3 ]