[ CAS No. 77332-79-7 ] {[proInfo.proName]}

Name: 77332-79-7|3-Chloro-4-Iodopyridine|97%
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SKU: A152736
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Quality Control of [ 77332-79-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 77332-79-7 ]

CAS No. :	77332-79-7	MDL No. :	MFCD00272199
Formula :	C₅H₃ClIN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SQXBYRRNGPVSAU-UHFFFAOYSA-N
M.W :	239.44	Pubchem ID :	12602200
Synonyms :

Calculated chemistry of [ 77332-79-7 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.96
TPSA :	12.89 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) :	-6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.79
Log Po/w (XLOGP3) :	2.13
Log Po/w (WLOGP) :	2.34
Log Po/w (MLOGP) :	2.01
Log Po/w (SILICOS-IT) :	3.05
Consensus Log Po/w :	2.26

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.22
Solubility :	0.144 mg/ml ; 0.000601 mol/l
Class :	Soluble
Log S (Ali) :	-2.03
Solubility :	2.22 mg/ml ; 0.00929 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.6
Solubility :	0.0606 mg/ml ; 0.000253 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 77332-79-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 77332-79-7 ]

* 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 [ 77332-79-7 ]
Downstream synthetic route of [ 77332-79-7 ]

[ 77332-79-7 ] Synthesis Path-Upstream 1~6

1
[ 626-60-8 ]
[ 77332-79-7 ]

Yield	Reaction Conditions	Operation in experiment
0.5 g	Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -75℃; for 4 h; Stage #2: With iodine In tetrahydrofuran at -75℃; for 1 h;	To a cold solution of 3-chloro pyridine (1.0 g, 8.88 mmol) in THF (30.0 mL) was added LDA (5.9 mL, 8.88 mmol) at -75°C. The reaction mixture was stirred at -75°C for 4 h. Iodine (2.2 g, 8.88 mmol) was added and continued stirring at -75°C for 1 h. The reaction mixture was quenched in water at -70°C, extracted with ethyl acetate and concentrated to afford 0.500 g of desired product. ¹H NMR (300 MHz, DMSO d₆): δ 8.01 (d, J = 5.1 Hz, 1H), 8.14 (d, / = 4.8 Hz, 1H), 8.63 (s, 1H).

Reference： [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 5, p. 888 - 890
[2] Tetrahedron Letters, 2004, vol. 45, # 42, p. 7873 - 7877
[3] Tetrahedron, 1993, vol. 49, # 1, p. 49 - 64
[4] Patent: US6169086, 2001, A,
[5] Patent: WO2008/57209, 2008, A1, . Location in patent: Page/Page column 54-55
[6] Patent: WO2008/18639, 2008, A2, . Location in patent: Page/Page column 108-109
[7] Patent: WO2013/186692, 2013, A1, . Location in patent: Page/Page column 61; 62

2
[ 626-60-8 ]
[ 77332-79-7 ]
[ 77332-90-2 ]
[ 77332-89-9 ]
[ 77332-88-8 ]

Reference： [1] Tetrahedron Letters, 1980, vol. 21, # 43, p. 4137 - 4140
[2] Heterocycles, 1993, vol. 35, # 1, p. 151 - 169
[3] Heterocycles, 1993, vol. 35, # 1, p. 151 - 169
[4] Heterocycles, 1993, vol. 35, # 1, p. 151 - 169

3
[ 626-60-8 ]
[ 77332-79-7 ]
[ 77332-90-2 ]
[ 77332-89-9 ]
[ 77332-88-8 ]

4
[ 626-60-8 ]
[ 77332-79-7 ]
[ 77332-90-2 ]
[ 77332-89-9 ]
[ 77332-88-8 ]

5
[ 77332-79-7 ]
[ 81290-20-2 ]
[ 81565-19-7 ]

Reference： [1] European Journal of Organic Chemistry, 2004, # 18, p. 3793 - 3798

6
[ 77332-79-7 ]
[ 81565-19-7 ]

Reference： [1] Patent: WO2008/18639, 2008, A2, . Location in patent: Page/Page column 109

[ 77332-79-7 ] Synthesis Path-Downstream 1~72

1
[ 110-00-9 ]
[ 77332-79-7 ]
[ 40247-40-3 ]

Reference： [1]Heterocycles,1993,vol. 35,p. 151 - 169

2
[ 110-00-9 ]
[ 77332-79-7 ]
[ 40247-40-3 ]
[ 77332-86-6 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 4137 - 4140
[2]Heterocycles,1993,vol. 35,p. 151 - 169

3
[ 626-60-8 ]
[ 77332-79-7 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate C8: 3-Chloro-4-phenylpyridin-2-olStep 1 : 3-Chloro-4-iodopyridineThe title compound was prepared according to the following reference: 35 Heterocvcles 151-69 (1993). To a solution of DIPA (3.77 mL, 26.4 mmol) in THF (20 mL) under N2 in a dry ice bath, M-BuLi (10.6 mL, 26.4 mmol) was added. The mixture was stirred in an ice bath for 20 minutes, then treated dropwise over 10 minutes with a solution of 3-chloropyridine (2.51 mL, 26.4 mmol) in 5 mL THF, keeping the temperature less than -70C. The lithiopyridine partially precipitated as a colorless solid in a light orange solution. The mixture was stirred for 30 minutes in a dry ice bath, and then I2 (6.71 g, 26.4 mmol) in 15 mL THF was added, keeping the temperature less then -650C. The solution was then allowed to warm to O0C and was placed in an ice bath for 2 hours, and then poured into 10% NaHSO3 and extracted with ether (150 mL; 3x). The organics were washed with 50 mL each OfNaHSO3, NaHCO3, H2O, and brine. The residue was purified on SiO2 (gradient elution, 2-20% EtOAc/hexanes) to give the title compound (3.35 g, 85% pure). This was then recrystallized EPO <DP n="56"/>from hot hexanes plus a few mL of EtOAc to dissolve initially to give the title compound as a white powder (1.95 g). LRMS ESf (M+H)+ 240.0.
		(A) Synthesis of 3-chloro-4-trifluoromethylpyridine-2- carboxylic acid; <n="110"/>(1) 3-Chloro-4-iodopyridine was obtained from 3-chloropgammaridine by the method described in Tetrahedron (1993.) 49 (1), 49.
0.5 g		To a cold solution of 3-chloro pyridine (1.0 g, 8.88 mmol) in THF (30.0 mL) was added LDA (5.9 mL, 8.88 mmol) at -75C. The reaction mixture was stirred at -75C for 4 h. Iodine (2.2 g, 8.88 mmol) was added and continued stirring at -75C for 1 h. The reaction mixture was quenched in water at -70C, extracted with ethyl acetate and concentrated to afford 0.500 g of desired product. 1H NMR (300 MHz, DMSO d6): delta 8.01 (d, J = 5.1 Hz, 1H), 8.14 (d, / = 4.8 Hz, 1H), 8.63 (s, 1H).

With n-butyllithium; iodine; diisopropylamine; sodium sulfite; In tetrahydrofuran; hexane;

1) Preparation of 3-Chloro-4-iodopyridine To 76 ml of an anhydrous THF solution of 10 ml of diisopropylamine was added 48.6 ml (1.57 M hexane solution) of n-butyllithium at -78 C., and the mixture was stirred at that temperature for 30 minutes. To the reaction mixture was added 10 ml of a THF solution of 8.66 g of 3-chloropyridine, followed by stirring at -78 C. for 30 minutes. To the reaction mixture was further added 30 ml of a THF solution of 19.4 g of iodine, followed by stirring at the same temperature for 30 minutes. The temperature was raised to 0 C., at which the mixture was stirred for 2.5 hours. The reaction mixture was poured into 300 ml of a 8% sodium sulfite aqueous solution and extracted with diethyl ether. The organic layer was washed successively with a 10% sodium hydrogencarbonate aqueous solution, water, and a saturated sodium chloride aqueous solution and dried. The solvent was evaporated, and the residue was subjected to silica gel column chromatography using a mixture of ethyl acetate and hexane (1:9 by volume) as a developing solution. The fraction containing the desired compound was concentrated to give 4.54 g of the title compound. 1H-NMR (CDCl3) delta: 7.80 (d, 1H, J=5 Hz), 8.07 (d, 1H, J=5 Hz), 8.56 (s, 1H).

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 888 - 890
[2]Tetrahedron Letters,2004,vol. 45,p. 7873 - 7877
[3]Tetrahedron,1993,vol. 49,p. 49 - 64
[4]Patent: WO2008/57209,2008,A1 .Location in patent: Page/Page column 54-55
[5]Patent: WO2008/18639,2008,A2 .Location in patent: Page/Page column 108-109
[6]Patent: WO2013/186692,2013,A1 .Location in patent: Page/Page column 61; 62
[7]Patent: US6169086,2001,A

5
[ 625-86-5 ]
[ 77332-79-7 ]
[ 40247-42-5 ]

Reference： [1]Heterocycles,1993,vol. 35,p. 151 - 169

6
[ 77332-79-7 ]
[ 146140-95-6 ]
2,2-dimethyl-N-(2-(3-chloro-4-pyridyl)phenyl)propanamide [ No CAS ]

Reference： [1]Tetrahedron,1993,vol. 49,p. 49 - 64

8
[ 77332-79-7 ]
[ 81290-20-2 ]
[ 81565-19-7 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 3793 - 3798

9
[ 77332-79-7 ]
[ 81565-19-7 ]

Yield	Reaction Conditions	Operation in experiment
		(2) 3-Chloro-4-trifluoromethylpyridine was obtained from 3- chloro-4-iodopgammaridine by the method described in Eur. J. Org. Chem., (2004), 3793.

Reference： [1]Patent: WO2008/18639,2008,A2 .Location in patent: Page/Page column 109

10
[ 77332-79-7 ]
5-chloro-4-(trifluoromethyl)pyridine-2-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 3793 - 3798

11
[ 77332-79-7 ]
3-chloro-4-(trifluoromethyl)pyridine-2-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 3793 - 3798

12
[ 77332-79-7 ]
5-chloro-4-(trifluoromethyl)pyridine-3-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 3793 - 3798

13
[ 77332-79-7 ]
[ 796090-26-1 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 3793 - 3798

14
[ 77332-79-7 ]
[ 796090-30-7 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 3793 - 3798

15
[ 77332-79-7 ]
[ 796090-29-4 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 3793 - 3798

16
[ 77332-79-7 ]
[ 1026008-61-6 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 3793 - 3798

17
[ 77332-79-7 ]
[ 1026187-48-3 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 3793 - 3798

18
[ 77332-79-7 ]
[ 98-80-6 ]
[ 90732-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; at 95℃; for 18h;	Step 2: 3-Chloro-4-phenylpyridineTo a solution of the product from Step 1 (1.3 g, 5.43 mmol), phenylboronic acid(827 mg, 6.79 mmol), PCy3 (228 mg, 0.814 mmol), and Cs2CO3 (4.25 g, 13.03 mmol) in dioxane (10 mL), Pd2(dba)3 (497 mg, 0.543 mmol) was added under N2. The mixture was then heated to 95C for 18 hours, filtered and extracted with H2O and EtOAc. The organic layer was dried over MgSO4, and the solvent was removed in vacuo. The residue was purified on SiO2 (gradient elution, 5-30% EtOAc/hexanes) to give the title compound as a colorless oil (1.03 g). LRMS ESf (M+H)+ 190.2.

Reference： [1]Patent: WO2008/57209,2008,A1 .Location in patent: Page/Page column 55

19
C₁₁H₁₈BClN*Cl₂LiMg [ No CAS ]
[ 77332-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	With iodine;Inert atmosphere;	In each of the examples in Table 3, the substrate is reacted with the base in THF to form a metallic organoborate intermediate under the temperature and time conditions specified in Table 3. The metallic organoborate intermediate is then reacted with the electrophile, E, in THF to form the functionalized products 6a to 6g under the following conditions: Product 6g is obtained via iodolysis of the metallic organoborate intermediate.

Reference： [1]Patent: WO2012/85169,2012,A1 .Location in patent: Page/Page column 25-27

20
[ 77332-79-7 ]
[ 536-74-3 ]
[ 1439396-12-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; for 1h;Inert atmosphere; Reflux;	To a solution of <strong>[77332-79-7]3-chloro-4-iodopyridine</strong> (1 g, 4.2 mmol), 1-ethynylbenzene (430 mg, 4.2 mmol), and Pd(PPh3)2Cl2(147 mg, 0.21 mmol) in TEA (30 mL) was added Cul (40 mg, 0.21 mmol). The mixture was stirred at reflux for 60min.The reaction mixture was concentrated under reduced pressure and purified by flush column chromatography on silica gel (eluting with petroleum ether/ethyl acetate =100/1-5/1), to give the title product 3-chloro-4-(2- phenylethynyl)pyridine (0.85 g, 95%). 'HNMR: CDC13 400MHZ ? 8.67(s, 1H), 8.47~8.45(d, 1H, J=8), 7.70~7.68(m, 2H), 7.44~7.26(m, 4H).

Reference： [1]Patent: WO2013/78254,2013,A1 .Location in patent: Paragraph 00443

21
[ 77332-79-7 ]
[ 1439396-14-1 ]

Reference： [1]Patent: WO2013/78254,2013,A1

22
[ 77332-79-7 ]
[ 1439396-10-7 ]

Reference： [1]Patent: WO2013/78254,2013,A1

23
[ 77332-79-7 ]
C₂₄H₄₂BNO₄Si [ No CAS ]
[ 1448841-96-0 ]

Reference： [1]Heterocycles,2012,vol. 86,p. 1045 - 1054

24
[ 77332-79-7 ]
[ 1692-15-5 ]
3-chloro-4,4’-bipyridine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 2852 - 2855

25
[ 77332-79-7 ]
[ 1692-15-5 ]
3-chloro-1,1'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H,1'H-4,4'-bipyridinylidene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 2852 - 2855

26
[ 77332-79-7 ]
3-amino-5-chloropyrazine-2-thiol trifluoroacetate [ No CAS ]
6-chloro-3-((3-chloropyridin-4-yl)thio)pyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75 mg	With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105℃; for 10h;Inert atmosphere;	[00284] A solution of 3-amino-5-chloropyrazine-2-thiol (TFA salt: 0.158 g, 0.978 mmol) in dioxane (4.9 mL) was sparged with nitrogen for 10 min. Then, <strong>[77332-79-7]3-chloro-4-iodopyridine</strong> (0.468 g, 1.955 mmol), XantPhos (0.057 g, 0.098 mmol), Pd2(dba)3 (0.045 g, 0.049 mmol), and DIPEA (0.512 mL, 2.93 mmol) were added. The resulting mixture was stirred at 105 C for 10 h, filtered through Celite and concentrated. The crude was purified by silica chromatography (0 to 40% gradient of EtO Ac/heptane, containing 2% of Et3N) to afford 6-chloro-3-((3-chloropyridin-4- yl)thio)pyrazin-2-amine (75 mg, 0.274 mmol) as a white solid. NMR (400 MHz, CHLOROFORM-^ delta ppm 8.46 (s, 1 H), 8.22 (d, J=5.3 Hz, 1 H), 7.96 (s, 1 H), 6.68 (d, J=5.3 Hz, 1 H), 5.17 (br. s., 2 H). MS m/z 273.0 (M+H)+.
75 mg	With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105℃; for 10h;Inert atmosphere;	A solution of 3-amino-5-chloropyrazine-2-thiol(TFA salt: 0.158 g, 0.978 mmol) in dioxane (4.9 mE) wassparged with nitrogen for 10 mm. Then, 3-chloro-4-io-dopyridine (0.468 g, 1.955 mmol), XantPhos (0.057 g, 0.098mmol), Pd2(dba)3 (0.045 g, 0.049 mmol), and DIPEA (0.512 mE, 2.93 mmol) were added. The resulting mixture was stirred at 105 C. for 10 h, filtered through Celite and concentrated. The crude was purified by silica chromatography (0 to 40% gradient of EtOAc/heptane, containing 2% of Et3N) to afford 6-chloro-3-((3-chloropyridin-4-yl)thio) pyrazin-2-amine (75 mg, 0.274 mmol) as a white solid. ?H NMR (400 MHz, CHEOROFORM-d) oe ppm 8.46 (s, 1H),8.22 (d, J=5.3 Hz, 1H), 7.96 (s, 1H), 6.68 (d, J=5.3 Hz, 1H),5.17 (br. s., 2H). MS mlz 273.0 (M+H).
75 mg	With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105℃; for 10h;Inert atmosphere; Microwave irradiation;	A solution of 3-amino-5-chloropyrazine-2-thiol (TFA salt: 0.158 g, 0.978 mmol) in dioxane (4.9 mE) was sparged with nitrogen for 10 mm. Then, 3-chloro-4-io- dopyridine (0.468 g, 1.955 mmol), Xantphos (0.057 g, 0.098 mmol), Pd2(dba)3 (0.045 g, 0.049 mmol), and DIPEA (0.512 mE, 2.93 mmol) were added. The resulting mixture was stirred at 105 C. for 10 h, filtered through Celite and concentrated. The crude was purified by silica chromatography (0-40% gradient of EtOAc/heptane; heptane containing 2% of Et3N) to afford 6-chloro-3-((3-chioropyridin-4- yl)thio)pyrazin-2-amine (75 mg, 0.274 mmol) as a white solid. ?H NMR (400 MHz, CHLOROFORM-d) oe ppm 8.46 (s, 1H), 8.22 (d, J=5.3 Hz, 1H), 7.96 (s, 1H), 6.68 (d, J=5.3 Hz, 1H), 5.17 (bt s., 2H). MS mlz 273.0 (M+H).

Reference： [1]Patent: WO2015/107494,2015,A1 .Location in patent: Paragraph 00284
[2]Patent: US2017/1975,2017,A1 .Location in patent: Paragraph 0314; 0315
[3]Patent: US2017/15680,2017,A1 .Location in patent: Paragraph 0316; 0317

27
[ 77332-79-7 ]
3-amino-5-chloropyrazine-2-thiol trifluoroacetate [ No CAS ]
6-chloro-3-((3-chloropyridin-4-yl)thio)pyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75 mg	With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105℃; for 10h;Inert atmosphere;	A solution of 3-amino-5-chloropyrazine-2-thiol (TFA salt: 0.158 g, 0.978 mmol) in dioxane (4.9 mL) was sparged with nitrogen for 10 min. Then, <strong>[77332-79-7]3-chloro-4-iodopyridine</strong> (0.468 g, 1.955 mmol), Xantphos (0.057 g, 0.098 mmol), Pd2(dba)3 (0.045 g, 0.049 mmol), and DIPEA (0.512 mL, 2.93 mmol) were added. The resulting mixture was stirred at 105 C for 10 h, filtered throught Celite and concentrated. The crude was purified by silica chromatography (0- 40% gradient of EtO Ac/heptane; heptane containing 2% of Et3N) to afford 6-chloro-3-((3- chloropyridin-4-yl)thio)pyrazin-2-amine (75 mg, 0.274 mmol) as a white solid. NMR (400 MHz, CHLOROFORM-^ delta ppm 8.46 (s, 1 H), 8.22 (d, J=5.3 Hz, 1 H), 7.96 (s, 1 H), 6.68 (d, J=5.3 Hz, 1 H), 5.17 (br. s., 2 H). MS m/z 273.0 (M+H)+

Reference： [1]Patent: WO2015/107495,2015,A1 .Location in patent: Paragraph 00287

28
[ 77332-79-7 ]
2-{1-[4-(cyclopropylmethoxy)-2,6-difluorobenzyl]-1H-indazol-3-yl}-5-methoxypyrimidin-4-amine [ No CAS ]
N-(3-chloropyridin-4-yl)-2-{1-[4-(cyclopropylmethoxy)-2,6-difluorobenzyl]-1H-indazol-3-yl}-5-methoxypyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere;	1 .00 g (2.29 mmol) 2-{ 1 -[4-(cyclopropylmethoxy)-2,6-difluorobenzyl]- 1 H-indazol-3-yl}-5-methoxypyrimidin-4-amine 1-7-1, 602 mg (2.52 mmol) <strong>[77332-79-7]3-chloro-4-iodopyridine</strong>, 1.49 g(4.57 mmol) caesium carbonate, 51 mg (0.23 mmol) palladium acetate and 265 mg(0.46 mmol) 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were dissolved underinert atmosphere in 8.8 mL N,N-dimethylformamide. The suspension was heated to 100C for over night, cooled to room temperature and e xtracted with dichloromethane andwater. The organic layer was dried over sodium sulfate and concentrated underreduced pressure. The crude product was purified by crystallization to furnish 0.90 g (71% yield) of N-(3-chloropyridin-4-yl)-2-{ 1 -[4-(cyclopropylmethoxy)-2, 6-difluorobenzyl]-1 H-indazol-3-yl}-5-methoxypyrim idin-4-am me.1HNMR (400MHz, DMSO-d6): 6 [ppm]= 0.21 -0.37 (m, 2 H) 0.52 -0.57 (m, 2 H) 1.15-1.22 (m, 1 H) 3.83 (d, 2 H) 4.08(s,3 H) 5.68 (s,2 H) 6.80 (5, 1H) 6.82 (m, 2 H) 7.26 (t,1 H) 7.49 (t, 1 H) 7.85 (d, 1 H) 8.25 (5, 1 H) 8.35 - 8.57 (m, 2 H) 8.65 (br. s., 1 H) 8.97(d, 1 H).

Reference： [1]Patent: WO2016/42081,2016,A1 .Location in patent: Page/Page column 111

29
[ 77332-79-7 ]
N-(3-chloropyridin-4-yl)-2-{1-[4-(cyclopropylmethoxy)-2,6-difluorobenzyl]-1H-indazol-3-yl}-5-[3-(4-methylpiperazin-1-yl)propoxy]pyrimidin-4-amine [ No CAS ]

Reference： [1]Patent: WO2016/42081,2016,A1

30
[ 77332-79-7 ]
4-[(3-chloropyridin-4-yl)amino]-2-{1-[4-(cyclopropylmethoxy)-2,6-difluorobenzyl]-1H-indazol-3-yl}pyrimidin-5-ol [ No CAS ]

Reference： [1]Patent: WO2016/42081,2016,A1

31
[ 77332-79-7 ]
2-{1-[2,6-difluoro-4-(2-methoxyethoxy)benzyl]-1H-indazol-3-yl}-5-methoxypyrimidin-4-amine [ No CAS ]
2-(4-((3-(4-((2,6-dimethylpyrimidin-4-yl)amino)-5-methoxypyrimidin-2-yl)-1H-indazol-1-yl)methyl)-3,5-difluorophenoxy)ethanol [ No CAS ]
2-(1-(2,6-difluoro-4-(2-methoxyethoxy)benzyl)-1H-indazol-3-yl)-N-(2,6-dimethylpyrimidin-4-yl)-5-methoxypyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 105℃; for 16h;	Intermediate 1-9-1 Preparation of N-(3-chloropyridin-4-yl)-2-{1 -[2,6-difluoro-4-(2-met oxyet oxy)benzyl]- 1 /-/-indazol-3-yl}-5-met oxypyrimidin-4-amine 200 mg of 2-{1 -[2,6-Difluoro-4-(2-methoxyethoxy)benzyl]-1 /-/-indazol-3-yl}-5- methoxypyrimidin-4-amine 1 -8-1 (99 % pure, 0.45 mmol, 1 .0 eq.) was dissolved in 1 .7 mL DMF. 1 18 mg <strong>[77332-79-7]4-iodo-3-chloropyridine</strong> (CAS: 77332-79-7, 0.49 mmol, 1 .1 eq.), 438 mg cesium carbonate (1 .35 mmol, 3.0 eq.), 10 mg palladium(ll)acetate (0.045 mmol, 0.1 eq.) and 39 mg 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (0.067 mmol, 0.15 eq.) were added and the mixture was stirred at ^ 05qC for 16 h. The reaction mixture was diluted with water and dichloromethane. The layers were seperated and the aqueous layer was extracted with dichloromethane twice. The combined organic layers were dried using a waterresistant filter and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography to provide the analytically pure target comound: 177 mg, 0.32 mmol, 71 %. 1 H-NMR (300MHz, DMSO-de) : delta [ppm]= 3.25 (s, 3H), 3.55 - 3.66 (m, 2H), 4.00 - 4.17 (m, 5H), 5.68 (s, 2H), 6.73 - 6.91 (m, 2H), 7.25 (t, 1 H), 7.48 (t, 1 H), 7.85 (d, 1 H), 8.27 (s, 1 H), 8.38 (d, 1 H), 8.43 - 8.51 (m, 2H), 8.64 (s, 1 H), 8.96 (d, 1 H).

Reference： [1]Patent: WO2016/42084,2016,A1 .Location in patent: Page/Page column 113-114; 125-126; 144-145

32
[ 77332-79-7 ]
2-{1-[2,6-difluoro-4-(2-methoxyethoxy)benzyl]-1H-indazol-3-yl}-5-methoxypyrimidin-4-amine [ No CAS ]
N-(3-chloropyridin-4-yl)-2-{1-[2,6-difluoro-4-(2-methoxyethoxy)benzyl]-1H-indazol-3-yl}-5-methoxypyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 105℃; for 16h;	Intermediate 1-9-1 Preparation of N-(3-chloropyridin-4-yl)-2-{1 -[2,6-difluoro-4-(2-met oxyet oxy)benzyl]- 1 /-/-indazol-3-yl}-5-met oxypyrimidin-4-amine 200 mg of 2-{1 -[2,6-Difluoro-4-(2-methoxyethoxy)benzyl]-1 /-/-indazol-3-yl}-5- methoxypyrimidin-4-amine 1 -8-1 (99 % pure, 0.45 mmol, 1 .0 eq.) was dissolved in 1 .7 mL DMF. 1 18 mg <strong>[77332-79-7]4-iodo-3-chloropyridine</strong> (CAS: 77332-79-7, 0.49 mmol, 1 .1 eq.), 438 mg cesium carbonate (1 .35 mmol, 3.0 eq.), 10 mg palladium(ll)acetate (0.045 mmol, 0.1 eq.) and 39 mg 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (0.067 mmol, 0.15 eq.) were added and the mixture was stirred at ^ 05qC for 16 h. The reaction mixture was diluted with water and dichloromethane. The layers were seperated and the aqueous layer was extracted with dichloromethane twice. The combined organic layers were dried using a waterresistant filter and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography to provide the analytically pure target comound: 177 mg, 0.32 mmol, 71 %. 1 H-NMR (300MHz, DMSO-de) : delta [ppm]= 3.25 (s, 3H), 3.55 - 3.66 (m, 2H), 4.00 - 4.17 (m, 5H), 5.68 (s, 2H), 6.73 - 6.91 (m, 2H), 7.25 (t, 1 H), 7.48 (t, 1 H), 7.85 (d, 1 H), 8.27 (s, 1 H), 8.38 (d, 1 H), 8.43 - 8.51 (m, 2H), 8.64 (s, 1 H), 8.96 (d, 1 H).

Reference： [1]Patent: WO2016/42084,2016,A1 .Location in patent: Page/Page column 113-114

33
[ 77332-79-7 ]
(4,4-dimethylhept-1-en-6-yn-1-yl)(phenyl)sulfane [ No CAS ]
3-chloro-4-(4,4-dimethyl-7-(phenylthio)hept-6-en-1-yn-1-yl)pyridine [ No CAS ]
3-chloro-4-(4,4-dimethyl-7-(phenylthio)hept-6-en-1-yn-1-yl)pyridine [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 4104 - 4107

34
[ 77332-79-7 ]
[ 2926-30-9 ]
[ 749875-03-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tert.-butylhydroperoxide; In dichloromethane; water; at 20℃; for 12h;	To a 500 mL three-necked flask was added 250 mL of dichloromethane and 100 mL of water, and 50 g of <strong>[77332-79-7]3-chloro-4-iodopyridine</strong> (0.2 mol, 1.0 eq), 50 mL of t-butyl hydroperoxide and 180 g of sodium trifluoromethanesulfonate (1.0mol, 5eq). After the reaction was stirred at room temperature for 12 h, the methylene chloride was spin dried and slowly poured into crushed ice and stirred continuously. A large amount of white solid precipitated, filtered and the filter cake was washed three times with water. Dried and dried in vacuo to give 49 g of a white solid, 80% yield, 95% HPLC purity.

Reference： [1]Patent: CN107056689,2017,A .Location in patent: Paragraph 0019-0021; 0023-0025; 0027-0029

35
[ 77332-79-7 ]
C₂₇H₃₀BNO₄ [ No CAS ]
(E)-4-(2-(3-chloropyridin-4-yl)-1-(1H-indol-4-yl)-1-butenyl)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; In 2-methyltetrahydrofuran; water; at 75 - 80℃; for 8h;Inert atmosphere;	Under the nitrogen atmosphere,To (Z)-4-(1-(1-acetyl-indol-4-yl)-2- pinacolboronic acid-1-butenyl)benzaldehyde (1.8 g, 4 mmol)In a solution of 2-methyltetrahydrofuran (40 mL),<strong>[77332-79-7]3-chloro-4-iodopyridine</strong> (1.434 g, 6 mmol) was added in sequence,Aqueous KOH (1.5 mL, 24 mmol) and bis(triphenylphosphine)palladium dichloride (281 mg, 0.4 mmol),The reaction mixture is reacted at about 75-80C for about 8 h.Cool to room temperatureThe solvent is distilled off under reduced pressureThe resulting brown solid column chromatographic purificationObtained (E)-4-(2-(3-chloropyridin-4-yl)-1-(1H-indol-4-yl)-1-butenyl)benzaldehyde (1.1 g, 70% yield) ).

Reference： [1]Patent: CN107973780,2018,A .Location in patent: Paragraph 0181; 0194; 0195; 0196

36
[ 77332-79-7 ]
[ 205865-67-4 ]
2-(3-chloropyridin-4-yl)-2,2-difluoroacetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium fluoride; copper(l) iodide; In dimethyl sulfoxide; at 60℃; for 15h;Schlenk technique; Inert atmosphere;	2- (3-chloropyridin-4-yl) -2,2-difluoroacetic acid ethyl ester (compound 3c) was prepared according to the following procedure. In the Schlenk tube,3 - Chloro - 4 - iodopyridine (119.7 mg, 0.5 mmol), copper (I) iodide (190.5 mg, 1.0 mmol), potassium fluoride (58.1 mg, 1.0 mmol) and DMSO (2.0 mL).Finally, alpha- (trimethylsilyl) difluoroacetic acid ethyl ester (Compound 2a) (196.3 mg, 1.0 mmol) was added,Under a nitrogen atmosphere,And the mixture was stirred at 60 C. for 15 hours.After the reaction, trifluoroethanol (50.0 mg, 0.5 mmol) was added as an internal standard,As a result of measurement by 19 F-NMR, it was found that the objective product 2- (3-chloropyridin-4-yl) -2,2-difluoroacetic acid ethyl ester (compound 3c) was produced in 72% yield It was. The reaction mixture was extracted with ethyl acetate, washed with water and dried over anhydrous sodium sulfate. Anhydrous sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hexane: EtOAc = 30: 1, 20: 1, 20: 1) to give 2- (3-chloropyridin-4-yl) -2,2-difluoroacetic acid ethyl ester (Compound 3c) (70.8 mg, 0.30 mmol, yield: 60%).

Reference： [1]Patent: JP5679855,2015,B2 .Location in patent: Paragraph 0094-0096

37
[ 77332-79-7 ]
[ 36677-36-8 ]
C₁₉H₁₃N₃O [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1 .Location in patent: Paragraph 0142

38
[ 77332-79-7 ]
benzo[c]benzo[4,5]imidazo[1,2-a][1,6]naphthyridin-7-ol [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

39
[ 77332-79-7 ]
C₃₅H₂₁N₅O [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

40
[ 77332-79-7 ]
C₃₅H₁₉N₅OPd [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

41
[ 77332-79-7 ]
C₃₆H₂₀N₆O [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

42
[ 77332-79-7 ]
C₃₆H₁₈N₆OPd [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

43
[ 77332-79-7 ]
C₁₅H₁₀BrN₃O [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

44
[ 77332-79-7 ]
C₂₇H₂₇N₃O [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

45
[ 77332-79-7 ]
3-(2,6-diisopropylphenyl)benzo[c]imidazo[1,2-a][1,6]naphthyridin-11-ol [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

46
[ 77332-79-7 ]
C₄₃H₃₅N₅O [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

47
[ 77332-79-7 ]
C₄₃H₃₃N₅OPt [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

48
[ 77332-79-7 ]
C₅₃H₄₉N₅O [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

49
[ 77332-79-7 ]
C₅₃H₄₇N₅OPt [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

50
[ 77332-79-7 ]
C₃₁H₂₀N₆O [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

51
[ 77332-79-7 ]
C₃₁H₁₈N₆OPt [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

52
[ 77332-79-7 ]
C₃₁H₁₉N₅O [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

53
[ 77332-79-7 ]
C₃₁H₁₇N₅OPt [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

54
[ 77332-79-7 ]
C₁₄H₈BrN₃ [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

55
[ 77332-79-7 ]
C₂₆H₂₅N₃ [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

56
[ 77332-79-7 ]
C₅₆H₃₂Cl₂Ir₂N₁₂ [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

57
[ 77332-79-7 ]
C₄₂H₂₄IrN₉ [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

58
[ 77332-79-7 ]
[ 76875-21-3 ]
C₁₅H₁₁N₃O [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1 .Location in patent: Paragraph 0223

59
[ 77332-79-7 ]
C₉H₈BrN₃ [ No CAS ]
5-bromo-2-methylpyrazolo[1,5-a]pyrido[2,3-c][1,6]naphthyridine [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1 .Location in patent: Paragraph 0317

60
[ 77332-79-7 ]
[ 1286278-88-3 ]
2-bromopyrido[2,3-c]pyrrolo[1,2-a][1,6]naphthyridine [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1 .Location in patent: Paragraph 0352

61
[ 670-96-2 ]
[ 77332-79-7 ]
C₁₄H₉N₃ [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1 .Location in patent: Paragraph 0414

62
[ 77332-79-7 ]
[ 27305-70-0 ]
C₁₄H₁₀N₄ [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1 .Location in patent: Paragraph 0460

63
[ 77332-79-7 ]
[ 27305-70-0 ]
C₅₆H₃₆Cl₂Ir₂N₁₆ [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1

64
[ 17285-54-0 ]
[ 77332-79-7 ]
C₁₄H₉N₃ [ No CAS ]

Reference： [1]Patent: US2018/337349,2018,A1 .Location in patent: Paragraph 0489

65
[ 77332-79-7 ]
2-(phenanthren-9-yl)-1H-benzo[d]imidazole [ No CAS ]
C₂₆H₁₅N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 20 - 140℃; for 24h;Inert atmosphere;	To a flame-dried flask were addedPd(PPh3)4 (10 mol %). Xantphos (10 mol %), Cs2CO3 (3 eq)and 3-cffloro-4-iodopyridine (1.2 eq). Then, BimPhen (1 eq)and DMF (0.15 M) were added to the reaction mixture under the protection of N2. The reaction mixture was stirred for 10mm at room temperature, and then heated at 140 C. in apre-heated oil bath for 24 h. After that, the reaction mixturewas cooled to room temperature, diluted with CH2C12, filtered through a short pad of Celite, and washed with CH2C12. The combined organic extracts were concentratedunder reduced pressure and the resulting residue was pun-fled by colunm chromatography on silica gel to provide theproduct DFE-4 in 31% yield.

Reference： [1]Patent: US2018/334459,2018,A1 .Location in patent: Paragraph 0088

66
[ 77332-79-7 ]
2-(2,2,3,3,3-pentafluoropropoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyrazine [ No CAS ]
2-(3-chloropyridin-4-yl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.6%	With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; In 1,4-dioxane; water; at 60℃; for 2h;Inert atmosphere;	3-Chloro-4 iodopyridine (0.57 g, 2.381 mmol) was dissolved in dioxane (45 ml), and under nitrogen atmosphere,Bis (triphenylphosphine) palladium (II) dichloride (0.17 g, 0.24 mmol) was added at room temperature,And the temperature was raised to 60 C. after that,At 60 C., a solution of 2- (2,2,3,3,3-pentafluoropropoxy) -5- (4,4,5,5-tetramethyl-1,3,2 Dioxaborane-2-yl) pyrazine (1.1 g, 1.2 mmol) and 2 M aqueous sodium bicarbonate solution (6 ml) were added in that order, and the mixture was stirred for 2 hours. After cooling to room temperature, the solution was diluted with ethyl acetate and water and filtered using a filter aid to remove solid matter. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate, filtered, and the filtrate was evaporated under reduced pressure with an evaporator. The resulting crude product was purified by silica gel chromatography to give 2- (3-chloropyridin-4-yl) -5- (2,2,3,3,3-pentafluoropropoxy) pyrazine (0.39 g, 91.6%, brown oil)
91.6%	With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 - 60℃; for 2h;Inert atmosphere;	Dissolve <strong>[77332-79-7]3-chloro-4iodopyridine</strong> (0.57 g, 2.381 mmol) in dioxane (45 ml) and under nitrogen atmosphere,Add bis (triphenylphosphine) palladium (II) dichloride (0.17 g, 0.24 mmol) at room temperature,The temperature was raised to 60 C.after that,Manufactured at 60 C. in Synthesis Example 2-12- (2,2,3,3,3-pentafluoropropoxy) -5- (4,4,5,5-tetramethyl-1,3,2 dioxaborane-2-yl) pyrazine(1.1 g, 1.2 mmol),Add 2M aqueous sodium hydrogen carbonate solution (6 ml) sequentiallyStir for 2 hours. After cooling to room temperatureDilute with ethyl acetate and water and filter using a filter aid,The solids were removed. The filtrate is extracted twice with ethyl acetate,After drying with magnesium sulfate and filtration,The filtrate was evaporated under reduced pressure with an evaporator. The crude product obtained is purified by silica gel chromatography2- (3-Chloropyridin-4-yl) -5- (2,2,3,3,3-pentafluoropropoxy) pyrazine(0.39 g, 91.6%, brown oil) was obtained.

Reference： [1]Patent: JP2018/199664,2018,A .Location in patent: Paragraph 0258
[2]Patent: JP2019/19124,2019,A .Location in patent: Paragraph 0298

67
[ 77332-79-7 ]
[ 855-38-9 ]
(3-chloropyridin-4-yl)tris(4-methoxyphenyl)phosphonium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In chloroform at 20℃; for 36h;	General Procedure A: General procedure: An oven dried 8 mL vial (< 1.0 mmol) or 16 mL vial (1.0-4.0 mmol) equipped with a stir barwas charged with the iodopyridine (1.0 equiv) and (p-anisole)3P (1.0 equiv) and CHCl3 (0.5 M).The reaction was then stirred at the temperature indicated (rt, 50 οC or 80 οC) for the stated time.The reaction was then purified by diluting the crude reaction with CHCl3 and by crashing out inEt2O (100 mL per 1.0 mmol) at room temperature.

Reference： [1]Boyle, Benjamin T.; Koniarczyk, J. Luke; McNally, Andrew [Synlett, 2021, vol. 32, # 2, p. 215 - 218]

68
[ 77332-79-7 ]
ethyl 9-[4-(trifluoromethyl)phenyl]-9H-pyrido[3,4-b]indole-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 6 h / 60 °C / Inert atmosphere 2: tri tert-butylphosphoniumtetrafluoroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1,4-dioxane; water / 16 h / 25 - 140 °C / 750.08 Torr / Inert atmosphere

Reference： [1]Current Patent Assignee: MERCK KGAA; CANCER RESEARCH UK - WO2022/18072, 2022, A1

69
[ 77332-79-7 ]
9-[4-(trifluoromethyl)phenyl]-9H-pyrido[3,4-b]indole-6-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 6 h / 60 °C / Inert atmosphere 2: tri tert-butylphosphoniumtetrafluoroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1,4-dioxane; water / 16 h / 25 - 140 °C / 750.08 Torr / Inert atmosphere 3: sodium hydroxide; water; ethanol / 1.5 h / 60 °C

Reference： [1]Current Patent Assignee: MERCK KGAA; CANCER RESEARCH UK - WO2022/18072, 2022, A1

70
[ 77332-79-7 ]
[ 913835-93-5 ]
ethyl 4-chloro-3-(3-chloropyridin-4-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 60℃; for 6h; Inert atmosphere;	3-1 Example 3-1 : Synthesis of ethyl 4-chloro-3-(3-chloropyridin-4-yl)benzoate To a solution of [2-chloro-5-(ethoxycarbonyl)phenyl]boronicacid (500 mg; 2.19 mmol) in dioxane (5 ml) and water (0.5 ml) was added 3-chloro-4-iodopyridine (576 mg; 2.41 mmol), Pd(dppf)CI2 (0.22 mmol) and K2CO3 (605 mg; 4.38 mmol) and N2 was bubbled through the reaction. Then, the reaction mixture was stirred under N2 atmosphere at 60 °C for 6 hrs. The mixture was poured into water (10 ml), and then extracted with EA (8 ml*3). The combined organic phase was collected and evaporated under vacuum. The residue was purified by C18 column chromatography (ACN/H2O = 5% - 95%) and the purified product could be obtained. (570 mg; 1.83 mmol; 84 %; white solid). 1H NMR (400 MHz, CDCI3) δ 8.07 (dd, J = 8.4, 2.1 Hz, 1H), 7.93 (d, J = 2.0 Hz, 1 H), 7.59 (d, J = 8.4 Hz, 1 H), 7.24 (d, J = 4.9 Hz, 1 H), 4.39 (q, J = 7.1 Hz, 2H), 1.40 (t, J = 7.1 Hz, 3H).
84%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 60℃; for 6h; Inert atmosphere;	3-1 Example 3-1 : Synthesis of ethyl 4-chloro-3-(3-chloropyridin-4-yl)benzoate To a solution of [2-chloro-5-(ethoxycarbonyl)phenyl]boronicacid (500 mg; 2.19 mmol) in dioxane (5 ml) and water (0.5 ml) was added 3-chloro-4-iodopyridine (576 mg; 2.41 mmol), Pd(dppf)CI2 (0.22 mmol) and K2CO3 (605 mg; 4.38 mmol) and N2 was bubbled through the reaction. Then, the reaction mixture was stirred under N2 atmosphere at 60 °C for 6 hrs. The mixture was poured into water (10 ml), and then extracted with EA (8 ml*3). The combined organic phase was collected and evaporated under vacuum. The residue was purified by C18 column chromatography (ACN/H2O = 5% - 95%) and the purified product could be obtained. (570 mg; 1.83 mmol; 84 %; white solid). 1H NMR (400 MHz, CDCI3) δ 8.07 (dd, J = 8.4, 2.1 Hz, 1H), 7.93 (d, J = 2.0 Hz, 1 H), 7.59 (d, J = 8.4 Hz, 1 H), 7.24 (d, J = 4.9 Hz, 1 H), 4.39 (q, J = 7.1 Hz, 2H), 1.40 (t, J = 7.1 Hz, 3H).

Reference： [1]Current Patent Assignee: MERCK KGAA; CANCER RESEARCH UK - WO2022/18072, 2022, A1 Location in patent: Page/Page column 152
[2]Current Patent Assignee: MERCK KGAA; CANCER RESEARCH UK - WO2022/18072, 2022, A1 Location in patent: Page/Page column 152

71
[ 77332-79-7 ]
[ 214360-73-3 ]
4-(3-chloropyridin-4-yl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.18 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 4h;	Intermediate 1.1 : 4-(2,3-dimethvlpyridin-4-vl)aniline General procedure: [00187] A suspension of 4-bromo-2,3-dimethyl-pyridine (3.3 g, 18 mmol, CAS: 259807- 91-5), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3.9 g, 18 mmol, CAS: 214360-73-3), potassium carbonate (6.1 g, 44 mmol) and Pd(dppf)Ck (1.3 g, 1.8 mmol) in 1,4-dioxane (20 ml_) and water (3 mL) was heated at 70°C for 15 h. The reaction mixture was filtered through a pad of Celite and concentrated in vacuo. The crude product was purified by flash column chromatography (eluting 100% EtOAc) to provide the title compound (2.6 g). LCMS (Method 1): 0.64 min, 199.1 [M+H]+
0.18 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 4h;	Intermediate 1.1 : 4-(2,3-dimethvlpyridin-4-vl)aniline General procedure: [00187] A suspension of 4-bromo-2,3-dimethyl-pyridine (3.3 g, 18 mmol, CAS: 259807- 91-5), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3.9 g, 18 mmol, CAS: 214360-73-3), potassium carbonate (6.1 g, 44 mmol) and Pd(dppf)Ck (1.3 g, 1.8 mmol) in 1,4-dioxane (20 ml_) and water (3 mL) was heated at 70°C for 15 h. The reaction mixture was filtered through a pad of Celite and concentrated in vacuo. The crude product was purified by flash column chromatography (eluting 100% EtOAc) to provide the title compound (2.6 g). LCMS (Method 1): 0.64 min, 199.1 [M+H]+

Reference： [1]Current Patent Assignee: SANOFI - WO2021/239743, 2021, A1 Location in patent: Paragraph 00187-00188
[2]Current Patent Assignee: SANOFI - WO2021/239743, 2021, A1 Location in patent: Paragraph 00187-00188

72
[ 77332-79-7 ]
1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carbaldehyde [ No CAS ]
(rac)-(3-chloropyridin-4-yl)(1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With ethynylmagnesium bromide	112.1 (rac)-3-Chloro-4-(1-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl)ethyl)pyridine Step 1: (rac)-(3-Chloropyridin-4-yl)(1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl)methanol. To a solution of 3-chloro-4-iodopyridine (240 mg, 1.0 mmol, 1.0 equiv.) in anhydrous THF (10 mL, 0.1M) under nitrogen atmosphere EtMgBr (3.0 M in diethyl ether, 0.4 mL, 1.2 mmol, 1.2 equiv.) was added. The resulting mixture was stirred at room temperature for 30 min, and 1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carbaldehyde (Intermediate 6, 178 mg, 1 mmol, 1.0 equiv.) was added as a solution in anhydrous THF (1 mL) and stirred at room temperature for 1 h. The reaction was quenched with water (5 mL) and extracted with EtOAc (3*10 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford (3-chloropyridin-4-yl)(1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl)methanol (200 mg, 69% yield) as a brown oil. The material was carried forward to the next step without further purification. LCMS: ESI-MS m/z: 292.0 [M+H]+.
	Stage #1: 3-chloro-4-iodopyridine With ethynylmagnesium bromide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carbaldehyde In tetrahydrofuran at 20℃; for 1h;	112.1 Step 1: To a solution of 3-chloro-4-iodopyridine (240 mg, 1.0 mmol, 1.0 equiv.) in anhydrous THF (10 mL, 0.1M) under nitrogen atmosphere EtMgBr (3.0 M in diethyl ether, 0.4 mL, 1.2 mmol, 1.2 equiv.) was added. The resulting mixture was stirred at room temperature for 30 min, and 1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carbaldehyde (Intermediate 6, 178 mg, 1 mmol, 1.0 equiv.) was added as a solution in anhydrous THF (1 mL) and stirred at room temperature for 1 h. The reaction was quenched with water (5 mL) and extracted with EtOAc (3*10 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford (3-chloropyridin-4-yl)(1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl)methanol (200 mg, 69% yield) as a brown oil. The material was carried forward to the next step without further purification. LCMS: ESI-MS m/z: 292.0 [M+H]+.
	Stage #1: 3-chloro-4-iodopyridine With ethynylmagnesium bromide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carbaldehyde In tetrahydrofuran at 20℃; for 1h;	112.1 Step 1: To a solution of 3-chloro-4-iodopyridine (240 mg, 1.0 mmol, 1.0 equiv.) in anhydrous THF (10 mL, 0.1M) under nitrogen atmosphere EtMgBr (3.0 M in diethyl ether, 0.4 mL, 1.2 mmol, 1.2 equiv.) was added. The resulting mixture was stirred at room temperature for 30 min, and 1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carbaldehyde (Intermediate 6, 178 mg, 1 mmol, 1.0 equiv.) was added as a solution in anhydrous THF (1 mL) and stirred at room temperature for 1 h. The reaction was quenched with water (5 mL) and extracted with EtOAc (3*10 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford (3-chloropyridin-4-yl)(1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl)methanol (200 mg, 69% yield) as a brown oil. The material was carried forward to the next step without further purification. LCMS: ESI-MS m/z: 292.0 [M+H]+.

Reference： [1]Current Patent Assignee: NURA BIO - US2022/81417, 2022, A1
[2]Current Patent Assignee: NURA BIO - US2022/81417, 2022, A1 Location in patent: Paragraph 0694-0695
[3]Current Patent Assignee: NURA BIO - US2022/81417, 2022, A1 Location in patent: Paragraph 0694-0695

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Environmental hazards
Code	Phrase
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H401	Toxic to aquatic life
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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

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[ 77332-79-7 ] Synthesis Path-Upstream 1~6

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Chlorides

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Pyridines

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