[ CAS No. 1211526-51-0 ] {[proInfo.proName]}

Name: 1211526-51-0|5-Bromo-2-methyl-3-(trifluoromethyl)pyridine|95%
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Quality Control of [ 1211526-51-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1211526-51-0 ]

Product Details of [ 1211526-51-0 ]

CAS No. :	1211526-51-0	MDL No. :	MFCD18257687
Formula :	C₇H₅BrF₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BMJHZCUPYJAGGV-UHFFFAOYSA-N
M.W :	240.02	Pubchem ID :	72207178
Synonyms :

Calculated chemistry of [ 1211526-51-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.9
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) :	-5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.13
Log Po/w (XLOGP3) :	2.83
Log Po/w (WLOGP) :	4.32
Log Po/w (MLOGP) :	2.64
Log Po/w (SILICOS-IT) :	3.48
Consensus Log Po/w :	3.08

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.42
Solubility :	0.0923 mg/ml ; 0.000385 mol/l
Class :	Soluble
Log S (Ali) :	-2.76
Solubility :	0.418 mg/ml ; 0.00174 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.16
Solubility :	0.0167 mg/ml ; 0.0000697 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.8

Safety of [ 1211526-51-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1211526-51-0 ]

* 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.

Downstream synthetic route of [ 1211526-51-0 ]

[ 1211526-51-0 ] Synthesis Path-Downstream 1~50

1
[ 1211526-51-0 ]
[ 1888470-64-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / 1,4-dioxane / 18 h / 105 °C / Inert atmosphere; Sealed tube 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 4 h / 90 °C / Inert atmosphere; Sealed tube

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2016/44792, 2016, A1

2
[ 1211526-51-0 ]
[ 73183-34-3 ]
[ 1888460-27-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane at 105℃; for 18h; Inert atmosphere; Sealed tube;	4.68.1 Step 1 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3- (trifluoromethyl)pyridine To a solution of 5-bromo-2-methyl-3-(trifluoromethyl)pyridine (1.0 g, 4.17 mmol) in dioxane (20 mL) in a sealed tube was added 4,4,4’,5,5,5’5’-octamethyl-2-2’-bi(1,3,2-dioxaborolane) (1.59 g, 6.25 mmol) and KOAc (819 mg, 8.34 mmol). The reaction was degassed with argon for 5 minutes then Pd(PPH3)2Cl2 (0.0147 mg, 0.021 mmol) was added. The reaction was heated at 105oC for 18 h, cooled to RT, diluted with water (100 mL) and extracted with EA (3x75 mL). The combined organic layer were dried with MgSO4 and concentrated to a residue which was purified by chromatography eluted with EA/HEP (5:95 to 30:70) to give 2-methyl-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine (1.2 g, 100% yield) as a white solid. LCMS: MH+ 206 (converts to boronic acid on LCMS) and TR = 1.804 min.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2016/44792, 2016, A1 Location in patent: Page/Page column 156

3
[ 1402664-67-8 ]
[ 1211526-51-0 ]

Yield	Reaction Conditions	Operation in experiment
34.6%	With tert.-butylnitrite; copper(I) bromide In acetonitrile at 25℃; for 2h;	14-18 Example 14: Preparation of compound 5 (5-bromo-2-methyl-3-(trifluoromethyl)pyridine) The reaction route is as shown in formula (V), and compound 4 (700 g,About 3.97 mol) was added to 7 L of acetonitrile.Add copper bromide (980 g, 4.39 mol),Add tert-butyl nitrite (1260 g, 12.2 mol),RT reaction for 2h,EA extraction, backwashing, drying, spin drying, distillation,Get 330g of yellow oil product,That is, 5-bromo-2-methyl-3-(trifluoromethyl)pyridine, the yield was about 34.6%.

Reference： [1]Current Patent Assignee: BIDE PHARMATECH - CN109232399, 2019, A Location in patent: Paragraph 0048-0054

4
[ 1211526-51-0 ]
[ 122536-77-0 ]
[ 2409467-29-2 ]

Yield	Reaction Conditions	Operation in experiment
		R.13 Reference Example 13 Reference Example 13 Tert-butyl (R)-(1-(6-methyl-5-(trifluoromethyl)pyridin-3-yl)pyrrolidin-3-yl)carbamate According to a technique similar to Reference Example 4, the title compound (white crystals, 22 mg, 4.9%) was obtained using 5-bromo-2-methyl-3-(trifluoromethyl)pyridine (310 mg, 1.29 mmol) and tert-butyl (R)-pyrrolidin-3-ylcarbamate (289 mg, 1.55 mmol). 1H NMR (CDCl3, 400 MHz): δ = 1.46 (s, 9H), 1.9 - 2.1 (m, 1H), 2.2 - 2.4 (m, 1H), 2.5 - 2.6 (m, 3H), 3.20 (dd, 1H, J = 4, 10 Hz), 3.3 - 3.4 (m, 1H), 3.4 - 3.5 (m, 1H), 3.61 (dd, 1H, J = 6, 10 Hz), 4.40 (br s, 1H), 4.70 (br s, 1H), 7.00 (d, 1H, J = 3 Hz), 7.98 (d, 1H, J = 3 Hz).

Reference： [1]Current Patent Assignee: KINDAI UNIVERSITY; NIPPON CHEMIPHAR CO LTD; UNIVERSITY OF CALGARY - EP3950059, 2022, A1

5
[ 1211526-51-0 ]
[ 4637-24-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide at 140℃;	Synthesis of I-2k A mixture of 5-bromo-2-methyl-3-(trifluoromethyl)pyridine (25 g, 104.16 mmol, 1 eq) in DMF (300 mL) and DMF-DMA (269.10 g, 2.26 mol, 300 mL) was stirred at 140 °C for 18 hr. The reaction mixture was concentrated in vacuum to afford I-2k (30 g, crude) as a brown oil, which was used directly without further purification.
	In N,N-dimethyl-formamide at 140℃;	Synthesis of I-2k A mixture of 5-bromo-2-methyl-3-(trifluoromethyl)pyridine (25 g, 104.16 mmol, 1 eq) in DMF (300 mL) and DMF-DMA (269.10 g, 2.26 mol, 300 mL) was stirred at 140 °C for 18 hr. The reaction mixture was concentrated in vacuum to afford I-2k (30 g, crude) as a brown oil, which was used directly without further purification.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 101
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 101

6
[ CAS Unavailable ]
[ CAS Unavailable ]
[ 1211526-51-0 ]
[ 2851874-05-8 ]

Yield	Reaction Conditions	Operation in experiment
73.08 %	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine at 100℃;	Synthesis of I-2a To a solution of 5-bromo-2-methy1-3-(trifluoromethyl) pyridine (10.00 g, 41.663 mmol, 1.00 equiv), Pd(DtBPF)C12(L00 g, 4.1663 mmol, 0.10 equiv) in 500 mL EtOH was added TEA (5.00 g, 83.326 mmol, 2.00 equiv) in a pressure tank. The mixture was purged with nitrogen for 10 min and then was pressurized to 30 atm with carbon monoxide at 100 °C and stirred overnight. The reaction mixture was cooled to room temperature and filtered to remove insoluble solids. The resulting mixture was diluted with water (1 L). The resulting mixture was extracted with EtOAc (5 x 200 mL). The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (50: 1) to afford I-2a (7.1 g, 73.08%) as a brown liquid.
73.08 %	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine at 100℃;	Synthesis of I-2a To a solution of 5-bromo-2-methy1-3-(trifluoromethyl) pyridine (10.00 g, 41.663 mmol, 1.00 equiv), Pd(DtBPF)C12(L00 g, 4.1663 mmol, 0.10 equiv) in 500 mL EtOH was added TEA (5.00 g, 83.326 mmol, 2.00 equiv) in a pressure tank. The mixture was purged with nitrogen for 10 min and then was pressurized to 30 atm with carbon monoxide at 100 °C and stirred overnight. The reaction mixture was cooled to room temperature and filtered to remove insoluble solids. The resulting mixture was diluted with water (1 L). The resulting mixture was extracted with EtOAc (5 x 200 mL). The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (50: 1) to afford I-2a (7.1 g, 73.08%) as a brown liquid.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 088
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 088

7
[ 67-56-1 ]
[ 1211526-51-0 ]
[ 2089326-95-2 ]

Yield	Reaction Conditions	Operation in experiment
37.67 %	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium hydroxide In 1,4-dioxane at 80℃;	88 Synthesis of 88a To a stirred mixture of 5-bromo-2miethyl-3-(triiluoromethyl)pyridine (1 g, 4.166 mmol, 1 equiv) and Pd2(dba)s (0.38 g, 0.417 mmol, 0.1 equiv) in MeOH (5 ml.) were added dioxane (10 mL) and KQH (0.70 g, 12.498 mmol, 3 equiv) at room temperature under nitrogen atmosphere. To the above mixture was added t-Brettpkos (0.40 g, 0.833 mmol, 0.2 equiv) in one portion at room temperature. The final reaction mixture was irradiated with microwave radiation for 40 min at 80°C. The reaction was quenched with NH4CI (aq.) at room temperature. The resulting mixture was extracted with EtOAe (3 x50 mL). The combined organic layers were washed with water (3x50 mL), dried over anhydrous MajSCH. After filtration, the -filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with C H 2C 1?/M eO H:::40 : 1 to afford 88a (300 mg, 37,67%) as a colorless oil.
37.67 %	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium hydroxide In 1,4-dioxane at 80℃;	88 Synthesis of 88a To a stirred mixture of 5-bromo-2miethyl-3-(triiluoromethyl)pyridine (1 g, 4.166 mmol, 1 equiv) and Pd2(dba)s (0.38 g, 0.417 mmol, 0.1 equiv) in MeOH (5 ml.) were added dioxane (10 mL) and KQH (0.70 g, 12.498 mmol, 3 equiv) at room temperature under nitrogen atmosphere. To the above mixture was added t-Brettpkos (0.40 g, 0.833 mmol, 0.2 equiv) in one portion at room temperature. The final reaction mixture was irradiated with microwave radiation for 40 min at 80°C. The reaction was quenched with NH4CI (aq.) at room temperature. The resulting mixture was extracted with EtOAe (3 x50 mL). The combined organic layers were washed with water (3x50 mL), dried over anhydrous MajSCH. After filtration, the -filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with C H 2C 1?/M eO H:::40 : 1 to afford 88a (300 mg, 37,67%) as a colorless oil.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 360
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 360

8
[ 1211526-51-0 ]
[ 97674-02-7 ]
[ 2851876-82-7 ]

Yield	Reaction Conditions	Operation in experiment
83.05 %	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane at 100℃; Inert atmosphere;	101 Synthesis of 99k To a stirred solution of 98c (160 mg, 032 mmol, 1,0 equiv) and Pyridine (154 mg, 1.95 mmol, 6.0 equiv) in DCE (3 ml) was added tripliosgene (34mg. 0.11 tnmol, 0.35 equiv) at 0C under nitrogen atmosphere. The resulting mixture was stirred for 10 mm at room temperature under nitrogen atmosphere. The resulting mixture was washed with 3x10 m14 of sat. NaFICO3 (aq.) (10 ml). The resulting mixture was extracted with CH2Ch (3x10 mL). The combined organic layers were washed with water (3x1 0 mL) and dried over anhydrous CaCl2. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by Prep..TLC (CH2CI2/MeOH=i0:i) to afford Compound 98 (61 mg, 35%) as a yellow solid.LC-MS: (ES, m/z): [M+HV 518H-NME.: (400 MHz, drnso-d6, S ppm): 1.19 (s, 6H), 2.97 (s, 3H), 3.53 (s, 2H), 3.71 (s, 2H), 4.66 (s, 1H), 4.9 1-4.96 (m, 4H), 6.87-6.89 (d, 1H), 6.98 (s, 1H), 7.23 (s, 1H), 7.37-7.42 (m, 3H), 7.75-7.77 (m, 1H), 8.20 (s, 1H).
83.05 %	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane at 100℃; Inert atmosphere;	101 Synthesis of 99k To a stirred solution of 98c (160 mg, 032 mmol, 1,0 equiv) and Pyridine (154 mg, 1.95 mmol, 6.0 equiv) in DCE (3 ml) was added tripliosgene (34mg. 0.11 tnmol, 0.35 equiv) at 0C under nitrogen atmosphere. The resulting mixture was stirred for 10 mm at room temperature under nitrogen atmosphere. The resulting mixture was washed with 3x10 m14 of sat. NaFICO3 (aq.) (10 ml). The resulting mixture was extracted with CH2Ch (3x10 mL). The combined organic layers were washed with water (3x1 0 mL) and dried over anhydrous CaCl2. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by Prep..TLC (CH2CI2/MeOH=i0:i) to afford Compound 98 (61 mg, 35%) as a yellow solid.LC-MS: (ES, m/z): [M+HV 518H-NME.: (400 MHz, drnso-d6, S ppm): 1.19 (s, 6H), 2.97 (s, 3H), 3.53 (s, 2H), 3.71 (s, 2H), 4.66 (s, 1H), 4.9 1-4.96 (m, 4H), 6.87-6.89 (d, 1H), 6.98 (s, 1H), 7.23 (s, 1H), 7.37-7.42 (m, 3H), 7.75-7.77 (m, 1H), 8.20 (s, 1H).

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 408
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 408

9
[ 1211526-51-0 ]
[ 27490-33-1 ]
[ 1824304-07-5 ]

Yield	Reaction Conditions	Operation in experiment
48.97 %	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In toluene at 100℃; Inert atmosphere;	71 Synthesis of 71a To a stirred solution of 5-bfQmo~2~methyl-3-(tAiTuoromethyl)pyHdine (3 g, 12,499 mmol, 1 equiv) and (tributylstamiyl)meihanol (6.02 g, 18.748 mmol, 1.5 equiv) in toluene (30 ml., 281,967 mmol, 22.56 equiv) was added Pd(PPh})4 (0.29 g, 0.250 mmol, 0.02 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 4 h at 100CC under nitrogen atmosphere. The resulting mixture was diluted with water (50 mL), The aqueous layer was extracted with EtOAc (2x20 mL). The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EA~30:1 to afford 71a (1.3 g, 48.97%) as colorless oil.
48.97 %	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In toluene at 100℃; Inert atmosphere;	71 Synthesis of 71a To a stirred solution of 5-bfQmo~2~methyl-3-(tAiTuoromethyl)pyHdine (3 g, 12,499 mmol, 1 equiv) and (tributylstamiyl)meihanol (6.02 g, 18.748 mmol, 1.5 equiv) in toluene (30 ml., 281,967 mmol, 22.56 equiv) was added Pd(PPh})4 (0.29 g, 0.250 mmol, 0.02 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 4 h at 100CC under nitrogen atmosphere. The resulting mixture was diluted with water (50 mL), The aqueous layer was extracted with EtOAc (2x20 mL). The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EA~30:1 to afford 71a (1.3 g, 48.97%) as colorless oil.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 292
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 292

10
[ 1663-39-4 ]
[ 1211526-51-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
37.6 %	With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 100℃; Inert atmosphere;	92 Synthesis of 92a To a stirred solution of 5-bromo-2~methyb3-(irifluoromeihyl)pyridine (1 g, 4,166 mmol, 1 equiv) aiid tert-butyl prop-2-enoate (0.53 g, 4.166 mmol, 1 equiv) in DMF (10 ml,) were added Pd(OAc)?. (0.09 g, 0.417 mmol, 0.1 equiv), TEA (1.26 g, 12.498 mmol, 3 equiv) and P(o~Tol)3 (0,51 g, 1.666 mmol, 0.4 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred overnight at 1G0°C under nitrogen atmosphere. The reaction was quenched with Water/ice (30 mL) at room temperature. The aqueous layer was extracted with EtOAc (3x15 mL). The resulting mixture was concentrated under reduced pressure. The residue was purified by Prep-TLC (PE / EA 6: 1) to afford 92a (450 mg, 37.60%) as colorless oil.
37.6 %	With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 100℃; Inert atmosphere;	92 Synthesis of 92a To a stirred solution of 5-bromo-2~methyb3-(irifluoromeihyl)pyridine (1 g, 4,166 mmol, 1 equiv) aiid tert-butyl prop-2-enoate (0.53 g, 4.166 mmol, 1 equiv) in DMF (10 ml,) were added Pd(OAc)?. (0.09 g, 0.417 mmol, 0.1 equiv), TEA (1.26 g, 12.498 mmol, 3 equiv) and P(o~Tol)3 (0,51 g, 1.666 mmol, 0.4 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred overnight at 1G0°C under nitrogen atmosphere. The reaction was quenched with Water/ice (30 mL) at room temperature. The aqueous layer was extracted with EtOAc (3x15 mL). The resulting mixture was concentrated under reduced pressure. The residue was purified by Prep-TLC (PE / EA 6: 1) to afford 92a (450 mg, 37.60%) as colorless oil.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 371; 371
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 371; 371

11
[ 558-43-0 ]
[ 1211526-51-0 ]
[ 2851876-49-6 ]

Yield	Reaction Conditions	Operation in experiment
13 %	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium hydroxide at 80℃; Microwave irradiation;	98 Synthesis of 98a To a stirred solution of 48h (2 g, 3.675 mrnol, 1 .00 equiv) and tributyi(i - ethoxyethenyi)stannane (1.73 g. 4.777 mmoi, 1.3 equiv) in dioxane (20 mL) was added Pd(PPh3):i (0.42 g, 0.363 mmol, 0.10 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred overnight at 100 degrees C under nitrogen athiosphere. The resulting mixture was diluted with water (50 mL). The aqueous layer was extracted with EtOAc (2x50 mL), The residue was purified by silica gel column chromatography, eluted with CH2C12 /MeOH(12:1) to 96a(1.5 g. 75.47%) as a yellow solid.
13 %	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium hydroxide at 80℃; Microwave irradiation;	98 Synthesis of 98a To a stirred solution of 48h (2 g, 3.675 mrnol, 1 .00 equiv) and tributyi(i - ethoxyethenyi)stannane (1.73 g. 4.777 mmoi, 1.3 equiv) in dioxane (20 mL) was added Pd(PPh3):i (0.42 g, 0.363 mmol, 0.10 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred overnight at 100 degrees C under nitrogen athiosphere. The resulting mixture was diluted with water (50 mL). The aqueous layer was extracted with EtOAc (2x50 mL), The residue was purified by silica gel column chromatography, eluted with CH2C12 /MeOH(12:1) to 96a(1.5 g. 75.47%) as a yellow solid.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 392
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 392

12
[ 865245-32-5 ]
[ 1211526-51-0 ]
[ 2851879-84-8 ]

Yield	Reaction Conditions	Operation in experiment
81.29 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 80℃; Inert atmosphere;	186 Synthesis of 186a Into a 100 mL 3-necked round-bottom flask were added tert-butyl 2-(4, 4,5,5- tetramethyI-L3,2-diQxabGroIan-2-yi)-5,6-dibydro-4H-pyridine-l-earboxy1ale (2 g, 6.468 mmol, 1 equiv), dioxane (20 mL), H2O (5 mL), 5-bromo-2 -methyl-3- (mfIuoromeihyl)pyHdme (2.33 g, 9.702 mmol, 1.5 equiv), K3PO4(4,12 g, 19,404 mmol, 3 equiv), and Pd(dppf)Cl2 (0.71 g, 0.970 mmol, 0.15 equiv) at room temperature. The resulting mixture was stirred overnight at 80"C under nitrogen atmosphere. The reaction was quenched by fee addition of water (20 mL) at room temperature. The aqueous layer was extracted wife EtOAe (3x20 mL.). The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluted with PE / EA (10:1) to afford 186a (1.8 g, 81,29%) as a light brown solid.
81.29 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 80℃; Inert atmosphere;	186 Synthesis of 186a Into a 100 mL 3-necked round-bottom flask were added tert-butyl 2-(4, 4,5,5- tetramethyI-L3,2-diQxabGroIan-2-yi)-5,6-dibydro-4H-pyridine-l-earboxy1ale (2 g, 6.468 mmol, 1 equiv), dioxane (20 mL), H2O (5 mL), 5-bromo-2 -methyl-3- (mfIuoromeihyl)pyHdme (2.33 g, 9.702 mmol, 1.5 equiv), K3PO4(4,12 g, 19,404 mmol, 3 equiv), and Pd(dppf)Cl2 (0.71 g, 0.970 mmol, 0.15 equiv) at room temperature. The resulting mixture was stirred overnight at 80"C under nitrogen atmosphere. The reaction was quenched by fee addition of water (20 mL) at room temperature. The aqueous layer was extracted wife EtOAe (3x20 mL.). The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluted with PE / EA (10:1) to afford 186a (1.8 g, 81,29%) as a light brown solid.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 663
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 663

13
[ 212127-83-8 ]
[ 1211526-51-0 ]
[ 2851874-97-8 ]

Yield	Reaction Conditions	Operation in experiment
77.2 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane at 80℃; Inert atmosphere;	66 Synthesis of 66a Into a 20mL round-bottom flask were added 5-bromo-2-methyl-3- (trifluoromethyl)pyridine(L00 g, 4.166 mmol, 1.00 equlv), dloxane (8.00 mL),H2O(2.G0 mL), tert-butyl 3"(4,4,5,5-tetra.metbybl,3,2-dioxaborolan-2-yl)-2,5-dibydropyrrole-l- carboxylate(l ,23 g, 4.167 mmol, 1.00 equlv), Pd(dppf)Cl2(0J0 g, 0.417 mmol, 0.1 equiv) and ?(.77 g, 8.333 mmol, 2 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 5h at 80 degrees C under nitrogen atmosphere. The resulting mixture was diluted with water (50 mL), The aqueous layer was extracted with EtOAe (3x30 ml.). The resulting mixture was concentrated under vacuum. The residue was purified by Prep-TLC (PE/EtOAc 5: 1 ) to afford 66a (1.1 g, 77.20%) as a white solid.
77.2 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane at 80℃; Inert atmosphere;	66 Synthesis of 66a Into a 20mL round-bottom flask were added 5-bromo-2-methyl-3- (trifluoromethyl)pyridine(L00 g, 4.166 mmol, 1.00 equlv), dloxane (8.00 mL),H2O(2.G0 mL), tert-butyl 3"(4,4,5,5-tetra.metbybl,3,2-dioxaborolan-2-yl)-2,5-dibydropyrrole-l- carboxylate(l ,23 g, 4.167 mmol, 1.00 equlv), Pd(dppf)Cl2(0J0 g, 0.417 mmol, 0.1 equiv) and ?(.77 g, 8.333 mmol, 2 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 5h at 80 degrees C under nitrogen atmosphere. The resulting mixture was diluted with water (50 mL), The aqueous layer was extracted with EtOAe (3x30 ml.). The resulting mixture was concentrated under vacuum. The residue was purified by Prep-TLC (PE/EtOAc 5: 1 ) to afford 66a (1.1 g, 77.20%) as a white solid.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 282
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 282

14
[ 1251732-64-5 ]
[ 1211526-51-0 ]
[ 2851875-97-1 ]

Yield	Reaction Conditions	Operation in experiment
71.12 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 80℃; Inert atmosphere;	87 Synthesis of 87a Into a 20mL sealed tube were added 5-bromo-2-methyl-3-(triiluofomethyl)pyridine (1 .00 g, 4,166 mmol, LOO equiv), dioxane (8.00 mL), H?Q (2.00 mL), tert-butyl N-[4~ (4,4,5,5-te†fame†hyl-i,3,2~dioxabofolan~2-yl)cydohex-3~en-l-yl]carbamale (1.35 g, 4.176 mmol, 1.00 equiv), Pd(dppf)Cl2 (0.30 g, 0.417 mmol, 0.1 equiv), and K3PO4 (1.77 g, 8.333 mmol, 2 equiv) under nitrogen atmosphere, The resulting mixture was stirred for 6b a.t 80 degrees C under nitrogen atmosphere. The resulting mixture was diluted with water (30 mL). The aqueous layer was extracted with EtOAc (3x20 mL). The resulting mixture was concentrated under vacuum. The residue was purified by Prep-TLC (PE/EtOAc 3: 1) to afford 87a (1.1 g, 71.12%) as a colorless oil.
71.12 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 80℃; Inert atmosphere;	87 Synthesis of 87a Into a 20mL sealed tube were added 5-bromo-2-methyl-3-(triiluofomethyl)pyridine (1 .00 g, 4,166 mmol, LOO equiv), dioxane (8.00 mL), H?Q (2.00 mL), tert-butyl N-[4~ (4,4,5,5-te†fame†hyl-i,3,2~dioxabofolan~2-yl)cydohex-3~en-l-yl]carbamale (1.35 g, 4.176 mmol, 1.00 equiv), Pd(dppf)Cl2 (0.30 g, 0.417 mmol, 0.1 equiv), and K3PO4 (1.77 g, 8.333 mmol, 2 equiv) under nitrogen atmosphere, The resulting mixture was stirred for 6b a.t 80 degrees C under nitrogen atmosphere. The resulting mixture was diluted with water (30 mL). The aqueous layer was extracted with EtOAc (3x20 mL). The resulting mixture was concentrated under vacuum. The residue was purified by Prep-TLC (PE/EtOAc 3: 1) to afford 87a (1.1 g, 71.12%) as a colorless oil.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 353
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 353

15
[ 1211526-51-0 ]
[ 286961-14-6 ]
[ 2851875-17-5 ]

Yield	Reaction Conditions	Operation in experiment
70.11 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 80℃;	76 Synthesis of 76a Into a 20mL sealed tube were added 5-feromo-2-methyl-3-(trifiuQromethy)pyridine (1 .00 g, 4.166 mmol, LOO equiv), dioxane (8.00 mi,), H2O (2,00 ml,), tert-butyl 4-(4, 4,5,5- tetramethyl~1 ,3,2~dioxaborolan~2~yi)~3,6-dihydro~2H~pyridine~1 -carboxylate (1.29 g, 4.172 mmol, 1.00 equiv), Pd(dppf)Cl2(0.30 g, 0.4G7 mmol, 0.10 equiv), and K3Rq4(1.77 g, 8.333 mmol, 2.00 equiv) at room temperature. The resulting mixture was stirred for 6I1 at 80 degrees C under nitrogen atmosphere. The reaction was concentrated under reduced pressure. The residue was purified by Prep-TLC (PE/EtOAc 3:1) to afford 76a (1 g, 70.11%) as a white solid.
70.11 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 80℃;	76 Synthesis of 76a Into a 20mL sealed tube were added 5-feromo-2-methyl-3-(trifiuQromethy)pyridine (1 .00 g, 4.166 mmol, LOO equiv), dioxane (8.00 mi,), H2O (2,00 ml,), tert-butyl 4-(4, 4,5,5- tetramethyl~1 ,3,2~dioxaborolan~2~yi)~3,6-dihydro~2H~pyridine~1 -carboxylate (1.29 g, 4.172 mmol, 1.00 equiv), Pd(dppf)Cl2(0.30 g, 0.4G7 mmol, 0.10 equiv), and K3Rq4(1.77 g, 8.333 mmol, 2.00 equiv) at room temperature. The resulting mixture was stirred for 6I1 at 80 degrees C under nitrogen atmosphere. The reaction was concentrated under reduced pressure. The residue was purified by Prep-TLC (PE/EtOAc 3:1) to afford 76a (1 g, 70.11%) as a white solid.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 302
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 302

16
[ 1211526-51-0 ]
[ 286961-14-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
95.81 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 80℃; Inert atmosphere;	178 Synthesis of 175 To a sthed solution of 1 O7a (150 mg, 0.308 mmo1 LOO equiv) and (3S)-3- fluoropyrrolidine hydrochloride (115.93 mg, 0,924 mmol, 3 equiv) in T)CE (5 mL) were added TEA (93.42 mg, 0S24 mrnol, 3 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for Iii at room temperature. To the above mixture was added STAB (130.44 mg. 06i6 mmoi, 2 equiv) at room temperature. The resulting mixture was stirred for additional 3h at room temperature. The reaction was quenched by the addition of NH4.C1 (aq.) (20 mL) at room temperature. The aqueous layer was extracted with DCM (2x20 niL), The crude product (100 mg) was purified by Prep HPLC with the foflowing conditions (Column: XBridge Prep 0131) Ci 8 Column, 30*150 mm, 5arn; Mobile Phase A: Water( 10 rnrnol/L NH4HCO3), Mobile Phase B: ACN; Flow rate:60 rnL/rnin; Gradient: 25% B to 45% B in 7 mint Wave Length: 220 rim; RTI(rnin): 630) to afford 109 (33.7 mg, 1924%) as a yeflow solid.LC-MS: (ES, m/z): [M+H] 561H-NMR: (400 MHz, CD3OD, Sppm): 1.99-2.11 (m, 1H), 2.18-2.25 (m, 1H), 2.47-2.51 (m, 1H), 2.69-2.8 1 (m, 1H), 2.89-2.98 (m, 2H), 3.01 (s, 3H), 3.51 (s, 2H), 3.66 (s, 2H), 3.78 (s, 3H), 5.06 (s, 4H), 5.12-5.26 (m, 1H), 6.38 (s, 1H), 6.85-6.86 (m, 1H), 7.11-7.13 (m, 2H),7.25-7.26 (m, 1H), 7.70(s, 1H), 8.23 (s, 1H).
95.81 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 80℃; Inert atmosphere;	178 Synthesis of 175 To a sthed solution of 1 O7a (150 mg, 0.308 mmo1 LOO equiv) and (3S)-3- fluoropyrrolidine hydrochloride (115.93 mg, 0,924 mmol, 3 equiv) in T)CE (5 mL) were added TEA (93.42 mg, 0S24 mrnol, 3 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for Iii at room temperature. To the above mixture was added STAB (130.44 mg. 06i6 mmoi, 2 equiv) at room temperature. The resulting mixture was stirred for additional 3h at room temperature. The reaction was quenched by the addition of NH4.C1 (aq.) (20 mL) at room temperature. The aqueous layer was extracted with DCM (2x20 niL), The crude product (100 mg) was purified by Prep HPLC with the foflowing conditions (Column: XBridge Prep 0131) Ci 8 Column, 30*150 mm, 5arn; Mobile Phase A: Water( 10 rnrnol/L NH4HCO3), Mobile Phase B: ACN; Flow rate:60 rnL/rnin; Gradient: 25% B to 45% B in 7 mint Wave Length: 220 rim; RTI(rnin): 630) to afford 109 (33.7 mg, 1924%) as a yeflow solid.LC-MS: (ES, m/z): [M+H] 561H-NMR: (400 MHz, CD3OD, Sppm): 1.99-2.11 (m, 1H), 2.18-2.25 (m, 1H), 2.47-2.51 (m, 1H), 2.69-2.8 1 (m, 1H), 2.89-2.98 (m, 2H), 3.01 (s, 3H), 3.51 (s, 2H), 3.66 (s, 2H), 3.78 (s, 3H), 5.06 (s, 4H), 5.12-5.26 (m, 1H), 6.38 (s, 1H), 6.85-6.86 (m, 1H), 7.11-7.13 (m, 2H),7.25-7.26 (m, 1H), 7.70(s, 1H), 8.23 (s, 1H).

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 619
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 619

17
[ 1211526-51-0 ]
[ 79099-07-3 ]
[ 2851879-34-8 ]

Yield	Reaction Conditions	Operation in experiment
36.77 %	Stage #1: 5-bromo-2-methyl-3-(trifluoromethyl)pyridine With tert.-butyl lithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In tetrahydrofuran at -78℃; Inert atmosphere;	179 Synthesis of 179a To a sthed solution of 1 O7a (150 mg, 0.308 mmo1 LOO equiv) and (3S)-3- fluoropyrrolidine hydrochloride (115.93 mg, 0,924 mmol, 3 equiv) in T)CE (5 mL) were added TEA (93.42 mg, 0S24 mrnol, 3 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for Iii at room temperature. To the above mixture was added STAB (130.44 mg. 06i6 mmoi, 2 equiv) at room temperature. The resulting mixture was stirred for additional 3h at room temperature. The reaction was quenched by the addition of NH4.C1 (aq.) (20 mL) at room temperature. The aqueous layer was extracted with DCM (2x20 niL), The crude product (100 mg) was purified by Prep HPLC with the foflowing conditions (Column: XBridge Prep 0131) Ci 8 Column, 30*150 mm, 5arn; Mobile Phase A: Water( 10 rnrnol/L NH4HCO3), Mobile Phase B: ACN; Flow rate:60 rnL/rnin; Gradient: 25% B to 45% B in 7 mint Wave Length: 220 rim; RTI(rnin): 630) to afford 109 (33.7 mg, 1924%) as a yeflow solid.LC-MS: (ES, m/z): [M+H] 561H-NMR: (400 MHz, CD3OD, Sppm): 1.99-2.11 (m, 1H), 2.18-2.25 (m, 1H), 2.47-2.51 (m, 1H), 2.69-2.8 1 (m, 1H), 2.89-2.98 (m, 2H), 3.01 (s, 3H), 3.51 (s, 2H), 3.66 (s, 2H), 3.78 (s, 3H), 5.06 (s, 4H), 5.12-5.26 (m, 1H), 6.38 (s, 1H), 6.85-6.86 (m, 1H), 7.11-7.13 (m, 2H),7.25-7.26 (m, 1H), 7.70(s, 1H), 8.23 (s, 1H).
36.77 %	Stage #1: 5-bromo-2-methyl-3-(trifluoromethyl)pyridine With tert.-butyl lithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In tetrahydrofuran at -78℃; Inert atmosphere;	179 Synthesis of 179a To a sthed solution of 1 O7a (150 mg, 0.308 mmo1 LOO equiv) and (3S)-3- fluoropyrrolidine hydrochloride (115.93 mg, 0,924 mmol, 3 equiv) in T)CE (5 mL) were added TEA (93.42 mg, 0S24 mrnol, 3 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for Iii at room temperature. To the above mixture was added STAB (130.44 mg. 06i6 mmoi, 2 equiv) at room temperature. The resulting mixture was stirred for additional 3h at room temperature. The reaction was quenched by the addition of NH4.C1 (aq.) (20 mL) at room temperature. The aqueous layer was extracted with DCM (2x20 niL), The crude product (100 mg) was purified by Prep HPLC with the foflowing conditions (Column: XBridge Prep 0131) Ci 8 Column, 30*150 mm, 5arn; Mobile Phase A: Water( 10 rnrnol/L NH4HCO3), Mobile Phase B: ACN; Flow rate:60 rnL/rnin; Gradient: 25% B to 45% B in 7 mint Wave Length: 220 rim; RTI(rnin): 630) to afford 109 (33.7 mg, 1924%) as a yeflow solid.LC-MS: (ES, m/z): [M+H] 561H-NMR: (400 MHz, CD3OD, Sppm): 1.99-2.11 (m, 1H), 2.18-2.25 (m, 1H), 2.47-2.51 (m, 1H), 2.69-2.8 1 (m, 1H), 2.89-2.98 (m, 2H), 3.01 (s, 3H), 3.51 (s, 2H), 3.66 (s, 2H), 3.78 (s, 3H), 5.06 (s, 4H), 5.12-5.26 (m, 1H), 6.38 (s, 1H), 6.85-6.86 (m, 1H), 7.11-7.13 (m, 2H),7.25-7.26 (m, 1H), 7.70(s, 1H), 8.23 (s, 1H).

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 626
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 626

18
[ 1211526-51-0 ]
[ 2851880-60-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C 3: pyridine / dichloromethane / 2 h / 0 °C
	Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C 4: pyridine / dichloromethane / 2 h / 0 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

19
[ 1211526-51-0 ]
[ 2851880-62-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C 3: pyridine / dichloromethane / 2 h / 0 °C 4: hydrogen; palladium diacetate; tetramethylethylenediamine / 1,4-dioxane / 80 °C / 7600.51 Torr / Autoclave
	Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C 4: pyridine / dichloromethane / 2 h / 0 °C 5: hydrogen; palladium diacetate; tetramethylethylenediamine / 1,4-dioxane / 80 °C / 7600.51 Torr / Autoclave

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

20
[ 1211526-51-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
78.75 %	With selenium(IV) oxide In 1,4-dioxane at 20℃; Inert atmosphere;	215.1 1. Synthesis of 215a To a stirred solution of 5-bfomo-2metliyl"3-(triiluoromethyl) pyridine (30 g, 124.988 mmol, 1 equiv) in 1,4-dioxane was added SeO?. (55.47 g, 499.952 mmol, 4 equiv) at room temperature under nitrogen atmosphere. The final reaction mixture was irradiated with microwave radiation for overnight at 120CC. The resulting mixture was filtered: the filter cake was washed with DCM (3x100 mL). The filtrate was concentrated under reduced pressure. The reaction was quenched by the addition of Water (500ml,) at room temperature. The aqueous layer was extracted with EtOAc (3x300 mL), The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EA (20: 1 ) to afford 215a (25 g, 78.75%) as a yellow oil.
78.75 %	With selenium(IV) oxide In 1,4-dioxane at 20℃; Inert atmosphere;	215.1 1. Synthesis of 215a To a stirred solution of 5-bfomo-2metliyl"3-(triiluoromethyl) pyridine (30 g, 124.988 mmol, 1 equiv) in 1,4-dioxane was added SeO?. (55.47 g, 499.952 mmol, 4 equiv) at room temperature under nitrogen atmosphere. The final reaction mixture was irradiated with microwave radiation for overnight at 120CC. The resulting mixture was filtered: the filter cake was washed with DCM (3x100 mL). The filtrate was concentrated under reduced pressure. The reaction was quenched by the addition of Water (500ml,) at room temperature. The aqueous layer was extracted with EtOAc (3x300 mL), The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EA (20: 1 ) to afford 215a (25 g, 78.75%) as a yellow oil.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 754
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 754

21
[ 1211526-51-0 ]
[ 2851874-29-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

22
[ 1211526-51-0 ]
[ 2851874-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

23
[ 1211526-51-0 ]
[ 2851874-31-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 4: hydrogen; palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C / 7600.51 Torr
	Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 5: hydrogen; palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C / 7600.51 Torr

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

24
[ 1211526-51-0 ]
[ 2851871-61-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 4: hydrogen; palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C / 7600.51 Torr 5: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C
	Multi-step reaction with 6 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 5: hydrogen; palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C / 7600.51 Torr 6: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

25
[ 1211526-51-0 ]
[ 1227489-83-9 ]

Yield	Reaction Conditions	Operation in experiment
69.45 %	With selenium(IV) oxide In 1,4-dioxane at 120℃;	Synthesis of I-2g A solution of 5-bromo-2-methyl-3-(trifluonnnethyl)pyridine (60 g, 249.976 mmol, 1 equiv) in dioxane (350 mL) was added SeO2 (69.35 g, 624.940 mmol, 2.5 equiv). The resulting mixture was stirred overnight at 120 degrees C. The resulting mixture was filtered, the filter cake was washed with EtOAc (3x50 mL). The filtrate was diluted with water (300 mL). The aqueous layer was extracted with EtOAc (3x100 mL). The residue was purified by silica gel column chromatography, eluted with PE / EA (50: 1) to afford I-2g (49 g, 69.45%) as a yellow oil.
	Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C
69.45 %	With selenium(IV) oxide In 1,4-dioxane at 120℃;	Synthesis of I-2g A solution of 5-bromo-2-methyl-3-(trifluonnnethyl)pyridine (60 g, 249.976 mmol, 1 equiv) in dioxane (350 mL) was added SeO2 (69.35 g, 624.940 mmol, 2.5 equiv). The resulting mixture was stirred overnight at 120 degrees C. The resulting mixture was filtered, the filter cake was washed with EtOAc (3x50 mL). The filtrate was diluted with water (300 mL). The aqueous layer was extracted with EtOAc (3x100 mL). The residue was purified by silica gel column chromatography, eluted with PE / EA (50: 1) to afford I-2g (49 g, 69.45%) as a yellow oil.

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 095; 096
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[3]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1 Location in patent: Paragraph 095; 096

26
[ 1211526-51-0 ]
[ 2851874-12-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sulfuric acid / 50 °C
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sulfuric acid / 50 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

27
[ 1211526-51-0 ]
[ 2851874-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 20 °C
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

28
[ 1211526-51-0 ]
[ 2851874-42-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 20 °C 3: pyridine / dichloromethane / 1 h / 0 °C
	Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 20 °C 4: pyridine / dichloromethane / 1 h / 0 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

29
[ 1211526-51-0 ]
[ 2851874-43-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 20 °C 3: pyridine / dichloromethane / 1 h / 0 °C 4: palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C
	Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 20 °C 4: pyridine / dichloromethane / 1 h / 0 °C 5: palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

30
[ 1211526-51-0 ]
[ 2851874-44-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 20 °C 3: pyridine / dichloromethane / 1 h / 0 °C 4: palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C 5: sodium tris(acetoxy)borohydride / 20 °C
	Multi-step reaction with 6 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 20 °C 4: pyridine / dichloromethane / 1 h / 0 °C 5: palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C 6: sodium tris(acetoxy)borohydride / 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

31
[ 1211526-51-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2.1: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3.1: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 4.1: hydrogen; palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C / 7600.51 Torr 5.1: triethylamine / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 5.2: 20 °C / Inert atmosphere
	Multi-step reaction with 6 steps 1.1: N,N-dimethyl-formamide / 18 h / 140 °C 2.1: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3.1: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4.1: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 5.1: hydrogen; palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C / 7600.51 Torr 6.1: triethylamine / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 6.2: 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

32
[ 1211526-51-0 ]
[ 2851874-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2.1: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3.1: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 4.1: hydrogen; palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C / 7600.51 Torr 5.1: triethylamine / 1,2-dichloro-ethane / 10 min / 20 °C / Inert atmosphere 5.2: 20 °C / Inert atmosphere
	Multi-step reaction with 6 steps 1.1: N,N-dimethyl-formamide / 18 h / 140 °C 2.1: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3.1: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4.1: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 5.1: hydrogen; palladium diacetate; tetramethylethylenediamine; catacxium A / 1,4-dioxane / 80 °C / 7600.51 Torr 6.1: triethylamine / 1,2-dichloro-ethane / 10 min / 20 °C / Inert atmosphere 6.2: 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

33
[ 1211526-51-0 ]
[ 2851880-58-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

34
[ 1211526-51-0 ]
[ 2851875-29-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sulfuric acid / 50 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 6 h / 80 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sulfuric acid / 50 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 6 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

35
[ 1211526-51-0 ]
[ 2851875-31-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sulfuric acid / 50 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 4: hydrogen; 10% Pd/C / methanol / 20 °C
	Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sulfuric acid / 50 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 5: hydrogen; 10% Pd/C / methanol / 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

36
[ 1211526-51-0 ]
[ 2851875-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sulfuric acid / 50 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 4: hydrogen; 10% Pd/C / methanol / 20 °C 5: hydrogenchloride / water / 80 °C / Inert atmosphere
	Multi-step reaction with 6 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sulfuric acid / 50 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 5: hydrogen; 10% Pd/C / methanol / 20 °C 6: hydrogenchloride / water / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

37
[ 1211526-51-0 ]
[ 2851875-35-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sulfuric acid / 50 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 4: hydrogen; 10% Pd/C / methanol / 20 °C 5: hydrogenchloride / water / 80 °C / Inert atmosphere 6: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C
	Multi-step reaction with 7 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sulfuric acid / 50 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 5: hydrogen; 10% Pd/C / methanol / 20 °C 6: hydrogenchloride / water / 80 °C / Inert atmosphere 7: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

38
[ 1211526-51-0 ]
[ 2851872-24-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sulfuric acid / 50 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 4: hydrogen; 10% Pd/C / methanol / 20 °C 5: hydrogenchloride / water / 80 °C / Inert atmosphere 6: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C 7: pyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
	Multi-step reaction with 8 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sulfuric acid / 50 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 5: hydrogen; 10% Pd/C / methanol / 20 °C 6: hydrogenchloride / water / 80 °C / Inert atmosphere 7: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C 8: pyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

39
[ 1211526-51-0 ]
[ 2851875-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

40
[ 1211526-51-0 ]
[ 2851875-91-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

41
[ 1211526-51-0 ]
[ 2851875-93-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 4: hydrogen; palladium diacetate; tetramethylethylenediamine / 1,4-dioxane / 80 °C / 7600.51 Torr
	Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 5: hydrogen; palladium diacetate; tetramethylethylenediamine / 1,4-dioxane / 80 °C / 7600.51 Torr

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

42
[ 1211526-51-0 ]
[ 2851878-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

43
[ 1211526-51-0 ]
[ 2851878-85-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C 3: pyridine / dichloromethane / 20 min / 0 - 20 °C
	Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C 4: pyridine / dichloromethane / 20 min / 0 - 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

44
[ 1211526-51-0 ]
[ 2851879-11-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 4: hydrogen; palladium diacetate; tetramethylethylenediamine / 1,4-dioxane / 80 °C / 7600.51 Torr 5: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C
	Multi-step reaction with 6 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 5: hydrogen; palladium diacetate; tetramethylethylenediamine / 1,4-dioxane / 80 °C / 7600.51 Torr 6: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

45
[ 1211526-51-0 ]
[ 2851879-13-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 4: hydrogen; palladium diacetate; tetramethylethylenediamine / 1,4-dioxane / 80 °C / 7600.51 Torr 5: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1 h / 20 °C
	Multi-step reaction with 6 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 5: hydrogen; palladium diacetate; tetramethylethylenediamine / 1,4-dioxane / 80 °C / 7600.51 Torr 6: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1 h / 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

46
[ 1211526-51-0 ]
[ 2851879-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sulfuric acid / 50 °C 3: Xantphos; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 100 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sulfuric acid / 50 °C 4: Xantphos; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

47
[ 1211526-51-0 ]
[ 2851879-65-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2.1: acetic acid / methanol / 1 h / 25 °C 2.2: 1 h / 25 °C
	Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide / 18 h / 140 °C 2.1: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3.1: acetic acid / methanol / 1 h / 25 °C 3.2: 1 h / 25 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

48
[ 1211526-51-0 ]
[ 2851873-32-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2.1: acetic acid / methanol / 1 h / 25 °C 2.2: 1 h / 25 °C 3.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide / 18 h / 140 °C 2.1: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3.1: acetic acid / methanol / 1 h / 25 °C 3.2: 1 h / 25 °C 4.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

49
[ 1211526-51-0 ]
[ 2851880-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 100 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

50
[ 1211526-51-0 ]
[ 2851880-09-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: selenium(IV) oxide / 1,4-dioxane / 120 °C 2: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 100 °C / Inert atmosphere 5: hydrogenchloride / tetrahydrofuran; water / 20 °C
	Multi-step reaction with 6 steps 1: N,N-dimethyl-formamide / 18 h / 140 °C 2: sodium periodate / tetrahydrofuran / 16 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 10 min / 0 - 20 °C / Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 100 °C / Inert atmosphere 6: hydrogenchloride / tetrahydrofuran; water / 20 °C

Reference： [1]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1
[2]Current Patent Assignee: HOTSPOT THERAPEUTICS - WO2022/221704, 2022, A1

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[ CAS No. 1211526-51-0 ] {[proInfo.proName]}

Quality Control of [ 1211526-51-0 ]

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[ 1211526-51-0 ] Synthesis Path-Downstream 1~50

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[ 1211526-51-0 ]

Fluorinated Building Blocks

Bromides

Trifluoromethyls

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[ 1211526-51-0 ]

Pyridines

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P311	Call a POISON CENTER or doctor/physician.
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P313	Get medical advice/attention.
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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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:
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P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
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.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
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.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 1211526-51-0 ] {[proInfo.proName]}

Quality Control of [ 1211526-51-0 ]

Related Doc. of [ 1211526-51-0 ]

Product Details of [ 1211526-51-0 ]

Calculated chemistry of [ 1211526-51-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1211526-51-0 ]

Application In Synthesis of [ 1211526-51-0 ]

[ 1211526-51-0 ] Synthesis Path-Downstream 1~50

Related Functional Groups of [ 1211526-51-0 ]

Fluorinated Building Blocks

Bromides

Trifluoromethyls

Related Parent Nucleus of [ 1211526-51-0 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1211526-51-0 ]

Related Parent Nucleus of
[ 1211526-51-0 ]