[ CAS No. 1776-37-0 ] {[proInfo.proName]}

Name: 1776-37-0|5-Methyl-1H-indazole|97%
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Quality Control of [ 1776-37-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1776-37-0 ]

Product Details of [ 1776-37-0 ]

CAS No. :	1776-37-0	MDL No. :	MFCD01606235
Formula :	C₈H₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DCUNRLLJHAWKRZ-UHFFFAOYSA-N
M.W :	132.16	Pubchem ID :	12639189
Synonyms :

Calculated chemistry of [ 1776-37-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.06
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) :	-5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.2
Log Po/w (XLOGP3) :	1.92
Log Po/w (WLOGP) :	1.87
Log Po/w (MLOGP) :	1.45
Log Po/w (SILICOS-IT) :	2.53
Consensus Log Po/w :	1.8

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.54
Solubility :	0.386 mg/ml ; 0.00292 mol/l
Class :	Soluble
Log S (Ali) :	-2.15
Solubility :	0.945 mg/ml ; 0.00715 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.26
Solubility :	0.0721 mg/ml ; 0.000546 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.06

Safety of [ 1776-37-0 ]

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

Application In Synthesis of [ 1776-37-0 ]

* 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 [ 1776-37-0 ]
Downstream synthetic route of [ 1776-37-0 ]

[ 1776-37-0 ] Synthesis Path-Upstream 1~9

1
[ 613-84-3 ]
[ 1776-37-0 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 39, p. 6890 - 6892

2
[ 95-68-1 ]
[ 1776-37-0 ]

Reference： [1] Liebigs Annalen der Chemie, 1980, # 6, p. 908 - 927
[2] Patent: WO2014/152144, 2014, A1,
[3] ChemMedChem, 2017, vol. 12, # 3, p. 257 - 270

3
[ 343770-79-6 ]
[ 1776-37-0 ]

Reference： [1] Liebigs Annalen der Chemie, 1980, # 6, p. 908 - 927

4
[ 2050-43-3 ]
[ 1776-37-0 ]

Reference： [1] Chemische Berichte, 1908, vol. 41, p. 663

5
[ 861779-89-7 ]
[ 1776-37-0 ]

Reference： [1] Chemische Berichte, 1920, vol. 53, p. 1213,1216, 1227

6
[ 6328-77-4 ]
[ 1776-37-0 ]

Reference： [1] Chemische Berichte, 1920, vol. 53, p. 1213,1216, 1227

7
[ 1201-24-7 ]
[ 1776-37-0 ]
[ 15719-64-9 ]

Reference： [1] Chemische Berichte, 1893, vol. 26, p. 218

8
[ 861779-89-7 ]
[ 71-43-2 ]
[ 1776-37-0 ]

Reference： [1] Chemische Berichte, 1920, vol. 53, p. 1213,1216, 1227

9
[ 7664-93-9 ]
[ 1776-37-0 ]

Reference： [1] Chemische Berichte, 1896, vol. 29, p. 308

[ 1776-37-0 ] Synthesis Path-Downstream 1~62

1
[ 74-96-4 ]
[ 1776-37-0 ]
2-ethyl-5-methyl-2H-indazole [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1924,vol. <2> 108,p. 314

2
[ 74-96-4 ]
[ 1776-37-0 ]
2-ethyl-5-methyl-2H-indazole [ No CAS ]
1-ethyl-5-methyl-1H-indazole [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1924,vol. <2> 108,p. 314

3
[ 1776-37-0 ]
[ 108-24-7 ]
[ 343770-79-6 ]

Reference： [1]Chemische Berichte,1920,vol. 53,p. 1213,1216, 1227

4
[ 1776-37-0 ]
[ 100-44-7 ]
2-benzyl-5-methyl-2H-indazole [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1924,vol. <2> 108,p. 314

5
[ 1776-37-0 ]
[ 123-62-6 ]
5-methyl-1-propionyl-1H-indazole [ No CAS ]

Reference： [1]Chemische Berichte,1920,vol. 53,p. 1213,1216, 1227

6
[ 1776-37-0 ]
[ 93-97-0 ]
1-benzoyl-5-methyl-1H-indazole [ No CAS ]

Reference： [1]Chemische Berichte,1920,vol. 53,p. 1213,1216, 1227

7
[ 1776-37-0 ]
[ 106-95-6 ]
2-allyl-5-methyl-2H-indazole [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1924,vol. <2> 108,p. 314

8
[ 1776-37-0 ]
[ 79-22-1 ]
5-methyl-indazole-1-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1924,vol. <2> 108,p. 314

9
[ 1776-37-0 ]
[ 74-88-4 ]
2,5-dimethyl-2H-indazole [ No CAS ]

Reference： [1]Chemische Berichte,1920,vol. 53,p. 1213,1216, 1227

10
[ 1776-37-0 ]
[ 74-88-4 ]
2,5-dimethyl-2H-indazole [ No CAS ]
[ 70127-93-4 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1924,vol. <2> 108,p. 314

11
[ 1776-37-0 ]
5-methyl-1-nitroso-1H-indazole [ No CAS ]

Reference： [1]Chemische Berichte,1896,vol. 29,p. 308

12
[ 1776-37-0 ]
[ 40598-72-9 ]

Reference： [1]Chemische Berichte,1922,vol. 55,p. 1141,1157

13
[ 2050-43-3 ]
[ 1776-37-0 ]

Reference： [1]Chemische Berichte,1908,vol. 41,p. 663

14
[ 861779-89-7 ]
[ 1776-37-0 ]

Reference： [1]Chemische Berichte,1920,vol. 53,p. 1213,1216, 1227

15
[ 1201-24-7 ]
[ 1776-37-0 ]
[ 15719-64-9 ]

Reference： [1]Chemische Berichte,1893,vol. 26,p. 218

16
[ 861779-89-7 ]
[ 71-43-2 ]
[ 1776-37-0 ]

Reference： [1]Chemische Berichte,1920,vol. 53,p. 1213,1216, 1227

17
[ 343770-79-6 ]
[ 1776-37-0 ]

Reference： [1]Liebigs Annalen der Chemie,1980,p. 908 - 927

18
2,4-dimethylbenzenediazonium tetrafluoroborate [ No CAS ]
[ 1776-37-0 ]

Yield	Reaction Conditions	Operation in experiment
1.0 g	With 18-crown-6 ether; potassium acetate; In chloroform; for 13h;Inert atmosphere;	0226] To a solution of 2,4-dimethylaniline (lOg) in 140ml HBF4 (40percent in H20) the solution of NaN02 (6.36g) in water was added at -10 °C slowly. A precipitate formed. The mixture turned red and was stirred for 1 h at 0 °C. The solid was filtered and washed with acetone and ethyl ether to give 2,4-dimethylbenzenediazonium tetrafluoroborate (5.25 g). The compound (5.25 g)was added to a mixture of ppotassium acetate (4.72 g) and 18-crown-6 (0.31 g) in 200 ml chloroform. The mixture was stirred under nitrogen atmosphere for 13 h and thereafter filtered. The filtrate was washed with water, dried over Na2S04, concentrated under vacuum to give 5 -methyl- lH-indazole (1.0 g).

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1063 - 1064
[2]Patent: WO2014/152144,2014,A1 .Location in patent: Paragraph 0226
[3]ChemMedChem,2017,vol. 12,p. 257 - 270

19
tert-butyl (2,4-dimethylphenyl)azo sulfide [ No CAS ]
[ 1776-37-0 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 3529 - 3536

20
[ 1776-37-0 ]
[ 76513-69-4 ]
5-Methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924

24
5-methyl-indazole-carboxylic acid-⁽³⁾ [ No CAS ]
[ 1776-37-0 ]

Reference： [1]Chemische Berichte,1893,vol. 26,p. 218

25
5-methyl-indazole-1-carboxylic acid methyl ester [ No CAS ]
alkaline solution [ No CAS ]
[ 1776-37-0 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1924,vol. <2> 108,p. 314

26
diazotized 7-amino-5-methyl-indazole [ No CAS ]
[ 1776-37-0 ]

Reference： [1]Chemische Berichte,1896,vol. 29,p. 308

27
diazotized asymm. m-xylidine [ No CAS ]
[ 1776-37-0 ]
3-(2,4-dimethyl-phenylazo)-5-methyl-1⁽²⁾H-indazole [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1899,vol. 305,p. 365

28
[ 7647-01-0 ]
[ 1776-37-0 ]
[ 7726-95-6 ]
[ 40598-72-9 ]

Reference： [1]Chemische Berichte,1922,vol. 55,p. 1141,1157

29
[ 1776-37-0 ]
[ 54255-11-7 ]
2-(4,5-dihydro-1H-imidazol-2-yl)-5-methyl-2H-indazol hydrochloride [ No CAS ]

Reference： [1]European Journal of Pharmaceutical Sciences,2003,vol. 20,p. 201 - 208

30
[ 613-84-3 ]
[ 1776-37-0 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 6890 - 6892

31
[ 1776-37-0 ]
[ 187274-94-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924

32
[ 1776-37-0 ]
(4R,5S,6S,7R)-4,7-Dibenzyl-5,6-dihydroxy-1,3-bis-(1H-indazol-5-ylmethyl)-[1,3]diazepan-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924

33
[ 1776-37-0 ]
(3aS,4R,8R,8aS)-4,8-Dibenzyl-2,2-dimethyl-5,7-bis-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-ylmethyl]-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924

34
[ 95-68-1 ]
[ 1776-37-0 ]

Reference： [1]Liebigs Annalen der Chemie,1980,p. 908 - 927
[2]Patent: WO2014/152144,2014,A1
[3]ChemMedChem,2017,vol. 12,p. 257 - 270

35
[ 6328-77-4 ]
[ 1776-37-0 ]

Reference： [1]Chemische Berichte,1920,vol. 53,p. 1213,1216, 1227

36
potassium borohydride [ No CAS ]
[ 1776-37-0 ]
thallium hydrotris(5-methylindazol-1-yl)borate [ No CAS ]

Reference： [1]Inorganic Chemistry,1997,vol. 36,p. 5097 - 5103

37
[ 1776-37-0 ]
[ 1034874-66-2 ]
[ 1034874-92-4 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3599 - 3608

38
[ 1776-37-0 ]
[ 885518-92-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 3h;	General procedure: 3-Iodoindazoles were obtained by direct iodination of commercial indazoles by the method previously described by Bocchi [28] with slight modifications. A solution of 1H-indazole (3 g, 25.4 mmol), iodine (12.7 g, 50.03 mmol) and potassium hydroxide (5.34 g, 95.25 mmol)in DMF (7 mL) was stirred for 3 h at room temperature. The reaction was quenched by dilution with saturated solution of sodium bisulfite (150 mL) and a precipitated was formed. The precipitated was filtered over vacuum and washed with water (3 × 30 mL). The solid was left to dry at 30 °C in a vacuum oven overnight obtaining 6.17 g of a pale yellow solid. Yield: 100percent; m.p.: 136?138 °C (lit.:[36] 134?136 °C); IR (KBr) nu (cm?1): 3086 (NH); 424 (C-I). 1H-NMR delta (ppm): 13.50 (1H, s, H-1); 7.55(1H, d, J = 8.6 Hz, H-7); 7.45?7.40 (2H, m, H-6 and H-4); 7.19 (1H, dd, J = 7.5 Hz, H-5). 13C-NMR delta(ppm): 140.41; 127.22; 126.79; 121.23; 120.39; 110.51; 93.49; HRMS calculated for C7H5IN2: 243.9497,Found: 243.9499.3-Iodo-1H-indazole (1a). 3-Iodoindazoles were obtained by direct iodination of commercial indazoles by the method previously described by Bocchi [28] with slight modifications. A solution of 1H-indazole(3 g, 25.4 mmol), iodine (12.7 g, 50.03 mmol) and potassium hydroxide (5.34 g, 95.25 mmol) in DMF(7 mL) was stirred for 3 h at room temperature. The reaction was quenched by dilution with saturated solution of sodium bisulfite (150 mL) and a precipitated was formed. The precipitated was filtered over vacuum and washed with water (3 30 mL). The solid was left to dry at 30 °C in a vacuum oven overnight obtaining 6.17 g of a pale yellow solid. Yield: 100percent; m.p.: 136?138 °C (lit.: [36] 134?136 °C)

Reference： [1]Molecules,2018,vol. 23
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6998 - 7003

39
[ 1776-37-0 ]
[Co(hydrotris(5-methylindazol-1-yl)borate)(hydrotris(3-neopentylpyrazol-1-yl)borate)] [ No CAS ]

Reference： [1]Inorganic Chemistry,1997,vol. 36,p. 5097 - 5103

40
[ 1776-37-0 ]
[Zn(hydrotris(5-methylindazol-1-yl)borate)2] [ No CAS ]

Reference： [1]Inorganic Chemistry,1997,vol. 36,p. 5097 - 5103

41
[ 1776-37-0 ]
[Fe(hydrotris(5-methylindazol-1-yl)borate)2] [ No CAS ]

Reference： [1]Inorganic Chemistry,1997,vol. 36,p. 5097 - 5103

42
[ 1776-37-0 ]
[Co(hydrotris(5-methylindazol-1-yl)borate)2] [ No CAS ]

Reference： [1]Inorganic Chemistry,1997,vol. 36,p. 5097 - 5103

43
[ 50342-08-0 ]
[ 1776-37-0 ]
C₁₂H₁₄N₄ [ No CAS ]
[ 1355356-65-8 ]

Yield	Reaction Conditions	Operation in experiment
27%		General procedure: Sodium hydride (0.53 g, 6.6 mmol, 60percent oil dispresion) was added to the stirred solution of the corresponding azole (3.3 mmol) in anhydrous THF (2 mL) at room temperature. After 15 min, freshly prepared 2-(chloromethyl)-4,5-dihydro-1H-imidazole 2 (0.47 g, 4.0 mmol) was added and the reaction mixture was stirred at ambient temperature for 6 h. The N-alkylation products 3, 5, 7 and 8 were isolated upon quenching the reaction mixture with water (5 mL) followed by extraction with dichloromethane (3 .x. 5 mL). The combined organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The oily residue thus obtained was purified on silica with use of chromatotron (Et3N/MeOH/AcOEt 1:5:100). All products were very polar with Rf values close to 0.05.The N-alkylation reaction of indazoles (1) provided the desired N1 substituted products (3) along with the N2 substituted side product. The latter compounds demonstrated considerably lower Rf than 3 and were not isolated in pure form. The alkylation reactions of benzotriazoles 6a and 6c allowed the isolation of N1 substituted products 7a-b (higher Rf) and N2 isomer 8b (lower Rf). However, in the case of 4-methyl-benzotriazole 6b only the N2 substituted isomer 8a was isolated as a pure product.The products 3, 5, 7 and 8 were then converted into water-soluble hydrochloride salts suitable for biological tests with use of methanolic hydrochloric acid solution or by passing gaseous hydrogen chloride through dichloromethane solution of the corresponding free base.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 108 - 116

44
[ 1776-37-0 ]
1-((4,5-dihydro-1H-imidazol-2-yl)methyl)-5-methyl-1H-indazole dihydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 108 - 116

45
[ 7436-90-0 ]
[ 1776-37-0 ]
[ 1373265-54-3 ]

Reference： [1]Organometallics,2012,vol. 31,p. 7933 - 7947

46
[ 29827-46-1 ]
[ 1776-37-0 ]
cis-[PdCl₂{C(5-methylindazole)=N(H)(cyclohexyl)}(CN(cyclohexyl))] [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 10394 - 10397

47
[ 1776-37-0 ]
[ 141699-59-4 ]
[ 1469326-84-8 ]

Yield	Reaction Conditions	Operation in experiment
1.04 g		To a solution of <strong>[1776-37-0]5-methylindazole</strong> (901 mg) in DMF (10 mL) was added sodium hydride (327 mg) at 0° C., and the mixture was stirred with heating at 40° C. for 30 minutes. To the reaction solution was added tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (2.28 g), and the mixture was stirred with heating at 90° C. for 19 hours. Then, the mixture was partitioned between ethyl acetate and water, and the organic layer was washed with brine and dried over Na2SO4. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:5 as the eluting solvent) to give Compound Q1 (1.04 g). [0225] 1H-NMR (400 MHz, CDCl3): 1.47 (9H, s), 2.00 (2H, m), 2.21 (2H, m), 2.43 (3H, s), 2.93 (2H, br), 4.28 (2H, br), 4.50 (1H, m), 7.19 (1H, d, J=8.0 Hz), 7.32 (1H, d, J=8.0 Hz), 7.48 (1H, s), 7.89 (1H, s)
1.04 g		in DMF solution of 5-methyl-indazole (901mg) (10mL) at 0 It was added sodium hydride (327 mg), heatedand stirred for 30 minutes at 40 ° C.. Thereafter,by adding to the reaction solution tert- butyl 4- (methylsulfonyloxy)piperidine-1-carboxylate (2.28 g) for 19 hours under heating and stirred at 90° C.. After completion of the reaction, ethyl acetate - toseparatory extraction with water, after which the resulting organic layer waswashed with saturated brine, and dried over sodium sulfate. The resultingresidue was purified by silica gel column chromatography (elution solvent;ethyl acetate: hexane = 2: 5) to give compound Q1 (1.04g) purified by

Reference： [1]Patent: US2014/121243,2014,A1 .Location in patent: Paragraph 0224; 0225
[2]Patent: JP2015/96495,2015,A .Location in patent: Paragraph 0118

48
[ 1776-37-0 ]
[ 1469326-85-9 ]

Reference： [1]Patent: US2014/121243,2014,A1

49
[ 1776-37-0 ]
N-(trans-4-methoxycyclohexyl)-4-(5-methyl-1H-indazol-1-yl)piperidine-1-carboxamide [ No CAS ]

Reference： [1]Patent: US2014/121243,2014,A1

50
[ 1776-37-0 ]
(S)-2-methyl-3-(5-methyl-1H-indazol-1-yl)propan-1-ol [ No CAS ]

Reference： [1]Patent: WO2014/152144,2014,A1

51
[ 1776-37-0 ]
(S)-2-methyl-3-(5-methyl-1H-indazol-1-yl)propyl methanesulfonate [ No CAS ]

Reference： [1]Patent: WO2014/152144,2014,A1

52
[ 1776-37-0 ]
1-((R)-3-(3-(cyclopropylmethoxy)-8-aza-bicyclo[3.2.1]octan-8-yl)-2-methylpropyl)-5-methyl-1H-indazole [ No CAS ]

Reference： [1]Patent: WO2014/152144,2014,A1

53
[ 1776-37-0 ]
[ 187756-76-9 ]
(S)-1-(3-((tert-butyldimethylsilyl)oxy)-2-methylpropyl)-5-methyl-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.12 g	With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 15h;	[0227] 5 -methyl- lH-indazole (760 mg), ((R)-3-bromo-2-methylpropoxy)(tert- butyl)dimethylsilane (1.59 g) and CsC03 were stirred in DMF at 50 °C for 15 h and thereafter the suspension was cooled to rt, water added and the mixture extracted with ethyl acetate and the combined organic layers washed with water and brine, dried over Na2S04, concentrated and purified by flash column chromatography (Si02: petroleum ether/ethyl acetate 20: 1), to give a colorless oil of (S)-l -(3 -((tert-butyldimethylsilyl)oxy)-2-methylpropyl)-5 -methyl- lH-indazole (l -12g).

Reference： [1]Patent: WO2014/152144,2014,A1 .Location in patent: Paragraph 0227

54
[ 1776-37-0 ]
N-(benzenesulfonyl)-N-[(trifluoromethyl)sulfanyl]benzenesulfonamide [ No CAS ]
5-methyl-1-(trifluoromethylthio)-1H-indazole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 7486 - 7509

55
[ 5153-67-3 ]
[ 1776-37-0 ]
(±)-5-methyl-1-(2-nitro-1-phenylethyl)-1H-indazole [ No CAS ]
5-methyl-2-(2-nitro-1-phenylethyl)-2H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; In diethyl ether; at 20 - 50℃; for 136h;	To a stirred suspension of (E)-(2-nitrovinyl)benzene (350 mg, 2.347 mmol) in Et20 (2 mL) was added 5 -methyl- lH-indazole (700 mg, 5.30 mmol) and iodine (596 mg, 2.347 mmol). The reaction mixture was stirred at room temperature for 5 days. LCMS showed the product. The reaction was heated at 50°C for 16 h. The mixture was quenched with water, washed with a mix of saturated sodium thiosulfate/NaHCOs (aq) (4/1) solution, extracted with DCM (100 mL><2). The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by column chromatography on silica gel Biotage 25M, eluting with 0, 2, 5,10 and 15percent EtOAc in Hexanes to give regioismer A (5-methyl-l-(2-nitro-l-phenylethyl)-lH- indazole) and regioisomer B (5-methyl-2-(2-nitro-l-phenylethyl)-2H-indazole). Step A, regioisomer A, LCMS calc. = 282.12, found = 282.05 (M+H)+. Step A, regioisomer B, LCMS calc. = 282.12, found = 282.04 (M+H)+.

Reference： [1]Patent: WO2016/94260,2016,A1 .Location in patent: Page/Page column 94

56
[ 1776-37-0 ]
(±)-2-(5-methyl-2H-indazol-2-yl)-2-phenylethanamine [ No CAS ]

Reference： [1]Patent: WO2016/94260,2016,A1

57
[ 1776-37-0 ]
(R)-2-chloro-N-(2-(5-methyl-2H-indazol-2-yl)-2-phenylethyl)-4-(4H-1,2,4-triazol-4-yl)benzamide [ No CAS ]
(S)-2-chloro-N-(2-(5-methyl-2H-indazol-2-yl)-2-phenylethyl)-4-(4H-1,2,4-triazol-4-yl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/94260,2016,A1

58
[ 1776-37-0 ]
(E)-5-(2-nitrovinyl)oxazole [ No CAS ]
(±)-5-(1-(5-methyl-1H-indazol-1-yl)-2-nitroethyl)oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 5 -methyl- lH-indazole (1.038 g, 7.85 mmol) in THF (24 mL) was added sodium hydride (0.428 g, 60percent in mineral oil, 10.71 mmol) at 0°C. The reaction mixture was stirred at 0°C for 10 min. To the reaction mixture was added (E)-5-(2-nitrovinyl)oxazole from step A (1 g, 7.14 mmol) in THF (6 mL) at 0°C. The reaction mixture was stirred at 0°C for 20 min. It was then quenched with saturated NH4C1 (aq) and extracted with EtOAc. The organic layer was dried over MgS04, filtered and concentrated. The crude material was purified by chromatography on silica gel (eluent: 0-50percent EtOAc in Hexanes). LCMS calc. = 273.09, found = 273.20 (M+H)+.

Reference： [1]Patent: WO2016/94260,2016,A1 .Location in patent: Page/Page column 96

59
[ 24424-99-5 ]
[ 1776-37-0 ]
2-methyl-2-propanyl 5-methyl-1H-indazole-1-carboxylate [ No CAS ]
2-methyl-2-propanyl 5-methyl-2H-indazole-2-carboxylate [ No CAS ]

Reference： [1]ChemMedChem,2017,vol. 12,p. 257 - 270

60
C₄₄H₄₁BF₁₀N₃P [ No CAS ]
[ 1776-37-0 ]
C₃₅H₃₁BF₁₀NP [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 6056 - 6068

61
[ 1776-37-0 ]
5-methyl-3-vinyl-1H-indazole [ No CAS ]

Reference： [1]Molecules,2018,vol. 23

62
[ 1776-37-0 ]
C₈H₁₀N₂ [ No CAS ]

Reference： [1]Science (Washington, DC, United States),2019,vol. 363,p. 838 - 845

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[ CAS No. 1776-37-0 ] {[proInfo.proName]}

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[ 1776-37-0 ] Synthesis Path-Upstream 1~9

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