[ CAS No. 161417-28-3 ] {[proInfo.proName]}

Name: 161417-28-3|4-Bromo-3-hydroxypyridine|98%
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Quality Control of [ 161417-28-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 161417-28-3 ]

SDS Specification

Alternatived Products of [ 161417-28-3 ]

Product Details of [ 161417-28-3 ]

CAS No. :	161417-28-3	MDL No. :	MFCD03093021
Formula :	C₅H₄BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YCVSFCXUHPVAFH-UHFFFAOYSA-N
M.W :	174.00	Pubchem ID :	2762429
Synonyms :

Calculated chemistry of [ 161417-28-3 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.96
TPSA :	33.12 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	1.19
Log Po/w (WLOGP) :	1.55
Log Po/w (MLOGP) :	0.58
Log Po/w (SILICOS-IT) :	1.64
Consensus Log Po/w :	1.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.22
Solubility :	1.04 mg/ml ; 0.00598 mol/l
Class :	Soluble
Log S (Ali) :	-1.48
Solubility :	5.74 mg/ml ; 0.033 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.3
Solubility :	0.876 mg/ml ; 0.00504 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.39

Safety of [ 161417-28-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 161417-28-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 161417-28-3 ]
Downstream synthetic route of [ 161417-28-3 ]

[ 161417-28-3 ] Synthesis Path-Upstream 1~3

1
[ 98976-81-9 ]
[ 161417-28-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium methylate In methanol	20c. 4-bromo-3-pyridinol To a solution of 4bromo-3-pyridyl diethylcarbamate (1.24 g, 4.50 mmol) in methanol (10 mL) was added sodium methoxide in methanol (2.04 g, 9.40 mmol), and the resultant mixture was refluxed for 1.5 hours. After removal of MeOH, EtOAc (15 mL) and water (1 mL) were added, the pH was then adjusted to 9 using 20percent H₂ SO₄. The organic layer was decanted, and the residue washed with EtOAc (3*5 mL). The combined organic layers were dried (Na₂ SO₄) and concentrated. The crude product was purified by flash chromatography on silica gel eluding with hexane/EtOAc (1:1 and 1:2) to provide 691 mg (89percent yield) of the title compound. TLC R_f 0.38 (1:2 hexane/EtOAc). MS (DCI/NH₃) m/e 174 with ⁷⁹ Br and 176 (M+H)⁺ with ⁸¹ Br. ¹ H NMR (CDCl₃, 300 MHz) δ: 8.43 (d, J =1.5 Hz, 1H, ArH), 8.02 (d, J=7.2 Hz, 1H, ArH), 7.54 (dd, J=7.2, 1.5 Hz, 1H, ArH).
89%	With sodium methylate In methanol	20c. 4bromo-3-pyridinol To a solution of 4-bromo-3-pyridyl diethylcarbamate (1.24 g, 4.50 mmol) in methanol (10 mL) was added sodium methoxide in methanol (2.04 g, 9.40 mmol), and the resultant mixture was refluxed for 1.5 hours. After removal of MeOH, EtOAc (15 mL) and water (1 mL) were added, the pH was then adjusted to 9 using 20percent H₂ SO₄. The organic layer was decanted, and the residue washed with EtOAc (3*5 mL). The combined organic layers were dried (Na₂ SO₄) and concentrated. The crude product was purified by flash chromatography on silica gel eluding with hexane/EtOAc (1:1 and 1:2) to provide 691 mg (89percent yield) of the title compound. TLC R_f 0.38 (1:2 hexane/EtOAc). MS (DCI/NH₃) m/e 174 with ⁷⁹ Br and 176 (M+H)⁺ with ⁸¹ Br. ¹ H NMR (CDCl₃, 300 MHz) δ: 8.43 (d, J=1.5Hz, 1H, ArH), 8.02 (d, J=7.2 Hz, 1H, ArH), 7.54 (dd, J=7.2, 1.5 Hz, 1H, ArH).

Reference： [1] Patent: US5914328, 1999, A,
[2] Patent: US5948793, 1999, A,

2
[ 10182-48-6 ]
[ 161417-28-3 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 1281,1286

3
[ 161417-28-3 ]
[ 19539-50-5 ]

Reference： [1] Patent: WO2018/71794, 2018, A1,

[ 161417-28-3 ] Synthesis Path-Downstream 1~88

1
[ 10182-48-6 ]
[ 161417-28-3 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1950,vol. 69,p. 1281,1286

2
[ 161417-28-3 ]
[ 69610-40-8 ]
(S)-2-(4-Bromo-pyridin-3-yloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 249 - 254

3
[ 161417-28-3 ]
[ 34381-71-0 ]
4-bromo-3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 249 - 254

4
[ 161417-28-3 ]
[ 66605-57-0 ]
[ 882170-26-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1679 - 1685

5
[ 161417-28-3 ]
(S)-1-Benzyl-2-[4-((Z)-2-pyridin-4-yl-vinyl)-pyridin-3-yloxy]-ethylamine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1679 - 1685

6
[ 161417-28-3 ]
{(S)-2-Phenyl-1-[4-((Z)-2-pyridin-4-yl-vinyl)-pyridin-3-yloxymethyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1679 - 1685

7
[ 161417-28-3 ]
4-bromo-3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 249 - 254

8
[ 161417-28-3 ]
[ 69610-40-8 ]
4-bromo-3-(2-(S)-pyrrolidinylmethoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With trifluoroacetic acid; In water;	20d. 4bromo-3-(2-(S)pyrrolidinylmethoxy)pyridine (S)-1-t-Butoxycarbonyl-2-pyrrolidinemethanol (792 mg, 3.94 mmol), <strong>[161417-28-3]4-bromo-3-pyridinol</strong> (685 mg, 3.94 mmol), DEAD (485 uL, 4.33 mmol) and PPh3 (1.14 g, 4.33 mmol) were allowed to react as described in Example 2a The crude product was directly treated with trifluoroacetic acid (5 mL) at room temperature for 3 hours. The trifluoroacetic acid was removed under reduced pressure, and water (8 mL) was added. The mixture was extracted with EtOAc (220 mL), and the resultant aqueous layer was basified with excess solid sodium bicarbonate. The resultant slurry was washed extensively with EtOAc (410 mL). The combined organic layers were dried (Na2 SO4) and evaporated. The crude product was purified by flash chromatography on silica gel eluding with CHCl3 /MeOH/NH4 OH (10:1.5:0.02 and 10:1.5:0.1) to provide 371 mg (37% yield from <strong>[161417-28-3]4bromo-3-pyridinol</strong>) of the title compound. TLC Rf 0.16 (10:1:0.02 CHCl3 /MeOH/NH4 OH). MS (DCI/NH3) m/e 257 with 79 Br and 259 (M+H)+with 81 Br. 1 H NMR (CDCl3, 300 MHz) 8: 8.25 (s, 1H, ArH), 8.08 (d, J=6.6 Hz, 1H, ArH), 7.48 (d, J=6.6 Hz, 1H, ArH), 4.28 (dd, J =4.8, 10.2 Hz, 1H, OCHH), 4.17 (dd, J=6.3, 10.2 Hz, 1H, OCHH), 3.90-3.80 (m, 1H, NCH), 3.30-3.14 (m, 2H, NCR2), 2.18-1.80 (m, 4H, 2CH2).
37%	With trifluoroacetic acid; In water;	20d. 4-bromo-3-(2-(S)-pyrrolidinylmethoxy)pyridine (S)-1-t-Butoxycarbonyl-2-pyrrolidinemethanol (792 mg, 3.94 mmol), <strong>[161417-28-3]4-bromo-3-pyridinol</strong> (685 mg, 3.94 mmol), DEAD (485 uL, 4.33 mmol) and PPh3 (1.14 g, 4.33 mmol) were allowed to react as described in Example 2a. The crude product was directly treated with trifluoroacetic acid (5 mL) at room temperature for 3 hours. The trifluoroacetic acid was removed under reduced pressure, and water (8 mL) was added. The mixture was extracted with EtOAc (220 mL), and the resultant aqueous layer was basified with excess solid sodium bicarbonate. The resultant slurry was washed extensively with EtOAc (410 mL). The combined organic layers were dried (Na2 SO4) and evaporated. The crude product was purified by flash chromatography on silica gel eluding with CHCl3 /MeOH/NH4 OH (10:1.5:0.02 and 10:1.5:0.1) to provide 371 mg (37% yield from <strong>[161417-28-3]4-bromo-3-pyridinol</strong>) of the title compound. TLC Rf 0.16 (10:1:0.02 CHCl3 /MeOH/NH4 OH). MS (DCI/NH3) m/e 257 with 79 Br and 259 (M+H)+ with 81 Br. 1 H NMR (CDCl3, 300 MHz) delta: 8.25 (s, 1H, ArH), 8.08 (d, J=6.6 Hz, 1H, ArH), 7.48 (d, J=6.6 Hz, 1H, ArH), 4.28 (dd, J=4.8, 10.2 Hz, 1H, OCHH), 4.17 (dd, J=6.3, 10.2 Hz, 1H, OCHH), 3.90-3.80 (m, 1H, NCH), 3.30-3.14 (m, 2H, NCH2), 2.18-1.80 (m, 4H, 2CH2).

Reference： [1]Patent: US5914328,1999,A
[2]Patent: US5948793,1999,A

9
[ 98976-81-9 ]
[ 161417-28-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium methylate; In methanol;	20c. 4-bromo-3-pyridinol To a solution of 4bromo-3-pyridyl diethylcarbamate (1.24 g, 4.50 mmol) in methanol (10 mL) was added sodium methoxide in methanol (2.04 g, 9.40 mmol), and the resultant mixture was refluxed for 1.5 hours. After removal of MeOH, EtOAc (15 mL) and water (1 mL) were added, the pH was then adjusted to 9 using 20% H2 SO4. The organic layer was decanted, and the residue washed with EtOAc (3*5 mL). The combined organic layers were dried (Na2 SO4) and concentrated. The crude product was purified by flash chromatography on silica gel eluding with hexane/EtOAc (1:1 and 1:2) to provide 691 mg (89% yield) of the title compound. TLC Rf 0.38 (1:2 hexane/EtOAc). MS (DCI/NH3) m/e 174 with 79 Br and 176 (M+H)+ with 81 Br. 1 H NMR (CDCl3, 300 MHz) delta: 8.43 (d, J =1.5 Hz, 1H, ArH), 8.02 (d, J=7.2 Hz, 1H, ArH), 7.54 (dd, J=7.2, 1.5 Hz, 1H, ArH).
89%	With sodium methylate; In methanol;	20c. 4bromo-3-pyridinol To a solution of 4-bromo-3-pyridyl diethylcarbamate (1.24 g, 4.50 mmol) in methanol (10 mL) was added sodium methoxide in methanol (2.04 g, 9.40 mmol), and the resultant mixture was refluxed for 1.5 hours. After removal of MeOH, EtOAc (15 mL) and water (1 mL) were added, the pH was then adjusted to 9 using 20% H2 SO4. The organic layer was decanted, and the residue washed with EtOAc (3*5 mL). The combined organic layers were dried (Na2 SO4) and concentrated. The crude product was purified by flash chromatography on silica gel eluding with hexane/EtOAc (1:1 and 1:2) to provide 691 mg (89% yield) of the title compound. TLC Rf 0.38 (1:2 hexane/EtOAc). MS (DCI/NH3) m/e 174 with 79 Br and 176 (M+H)+ with 81 Br. 1 H NMR (CDCl3, 300 MHz) delta: 8.43 (d, J=1.5Hz, 1H, ArH), 8.02 (d, J=7.2 Hz, 1H, ArH), 7.54 (dd, J=7.2, 1.5 Hz, 1H, ArH).

Reference： [1]Patent: US5914328,1999,A
[2]Patent: US5948793,1999,A

10
[ 161417-28-3 ]
[ 75-36-5 ]
[ 1219102-40-5 ]

Yield	Reaction Conditions	Operation in experiment
78.93%	With triethylamine; In dichloromethane; at 0 - 20℃; for 16.0h;	To a solution of <strong>[161417-28-3]4-bromopyridin-3-ol</strong> (5.0g, 28.74mmol, l .Oeq) in dichloromethane (75mL) was added dropwise triethylamine (11.61g, 114.96mmol, 4.0eq) followed by acetyl chloride (4.512g, 57.48mmol, 2.0eq) at 0C. The reaction mixture was stirred at room temperature for 16h. After completion of reaction, reaction mixture was filtered by bed of celite. The filtrate was transferred into water and extracted with ethyl acetate. Organic layer was combined, washed with brine, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography and compound was eluted on 5% ethyl acetate in hexane as eluent to obtain 198.1. (4.9g, 78.93%). MS(ES): m/z 217.03 [M+H]+

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 2227 - 2235
[2]Patent: WO2018/71794,2018,A1 .Location in patent: Paragraph 00915; 00916

11
C₁₀H₁₂BrNO₂ [ No CAS ]
[ 161417-28-3 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 2227 - 2235

12
[ 161417-28-3 ]
[ 1610521-15-7 ]

Reference： [1]Patent: WO2014/78257,2014,A1
[2]Patent: WO2014/140077,2014,A1
[3]Patent: WO2017/197056,2017,A1

13
[ 161417-28-3 ]
[ 1610519-86-2 ]

Reference： [1]Patent: WO2014/78257,2014,A1

14
[ 161417-28-3 ]
[ 7051-34-5 ]
[ 1610521-11-3 ]

Yield	Reaction Conditions	Operation in experiment
56%		Sodium hydride (288 mg, 7.23 mmol) was add to <strong>[161417-28-3]4-bromopyridin-3-ol</strong> (71-1) (1.05 g, 6.03 mmol) in DMF (30 mL) at 0 C and stirred for 1 hr. (bromomethyl)cyclopropane (71-2) (701 muL, 7.23 mmol) was added and the reaction stirred overnight at room temperature. Water was added (100 mL) and the reaction extracted with EtOAc (2 x 100 mL), washed with brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography (silica, 0- 10% MeOH in DCM) to give 4-bromo-3-(cyclopropylmethoxy)pyridine (71-3) (.766 g, 56%) of a brown oil. LC/MS (ES+): m/z 228.0 [M + H]+
44.6%		Sodium hydride (60% w/w) (1 10 mg, 2.76 mmol) was added to <strong>[161417-28-3]4-bromopyridin-3-ol</strong> (400 mg, 2.299 mmol) in DMF (15 mL) at 0C and left stirring for 30 minutes. (Bromomethyl)cyclopropane (0.268 mL, 2.76 mmol) was added and the reaction was warmed to rt and stirred overnight. Water was added (40 mL) and the organic product was extracted with EtOAc and washed with brine, dried through a hydrophobic frit and concentrated in vacuo. The residue was purified by silica gel column chromatography [0-5% MeOH/NH3 in DCM] and fractions containing product were combined and concentrated in vacuo to give the title compound as a brown oil (234 mg, 1.026 mmol, 44.6 % yield). LCMS (2 min, Formic Acid): Rt = 0.87 min, MH+ = 228/230.
44.6%		Sodium hydride (60 % w/w) (1 10 mg, 2.76 mmol) was added to <strong>[161417-28-3]4-bromopyridin-3-ol</strong> (400 mg, 2.299 mmol) in DMF (15 mL) at 0C and left stirring for 30 minutes. (Bromomethyl)cyclopropane (0.268 mL, 2.76 mmol) was added and the reaction was warmed to rt and stirred overnight. Water was added (40 mL) and the organic product was extracted with EtOAc and washed with brine, dried through a hydrophobic frit and concentrated in vacuo. The residue was purified by silica gel column chromatography [0-5 % MeOH/NH3 in DCM] and fractions containing product were combined and concentrated in vacuo to give 4-bromo-3-(cyclopropylmethoxy)pyridine (234 mg, 1.026 mmol, 44.6 % yield) as a brown oil. LCMS (2 min, Formic): Rt = 0.87 min, MhT = 228/230.

Reference： [1]Patent: WO2017/197056,2017,A1 .Location in patent: Page/Page column 400-401
[2]Patent: WO2014/78257,2014,A1 .Location in patent: Page/Page column 117
[3]Patent: WO2014/140077,2014,A1 .Location in patent: Page/Page column 51

15
[ 161417-28-3 ]
(R)-4-bromo-3-(oxetan-2-ylmethoxy)pyridine [ No CAS ]

Reference： [1]Patent: WO2014/140077,2014,A1

16
[ 161417-28-3 ]
7-(3-(cyclopropylmethoxy)pyridin-4-yl)-5-methyl-2-((4-(methylsulfonyl)piperazin-1-yl)methyl)furo[3,2-c]pyridin-4(5H)-one [ No CAS ]

Reference： [1]Patent: WO2014/140077,2014,A1

17
[ 161417-28-3 ]
(R)-7-(3-(cyclopropylmethoxy)pyridin-4-yl)-5-methyl-2-((2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)furo[3,2-c]pyridin-4(5H)-one [ No CAS ]

Reference： [1]Patent: WO2014/140077,2014,A1

18
[ 161417-28-3 ]
5-methyl-2-(((R)-2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)-7-(3-((R)-oxetan-2-ylmethoxy)pyridin-4-yl)furo[3,2-c]pyridin-4(5H)-one [ No CAS ]

Reference： [1]Patent: WO2014/140077,2014,A1

19
[ 161417-28-3 ]
oxetan-2-ylmethyl methanesulfonate [ No CAS ]
4-bromo-3-(oxetan-2-ylmethoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred suspension of <strong>[161417-28-3]4-bromopyridin-3-ol</strong> (300 mg, 1.724 mmol) in DMF (1 1 mL) was added sodium hydride (83 mg, 60% w/w, 2.069 mmol). This was cooled to 0C and left to stir for 30 min after which crude oxetan-2-ylmethyl methanesulfonate (for a preparation see Intermediate 66, 344 mg, 2.069 mmol) was added and the mixture was again left to stir for 4 h. All starting material remained so additional sodium hydride (60%) (83 mg, 2.069 mmol) was added and the mixture was cooled to 0C for 30 min before the addition of further crude oxetan-2-ylmethyl methanesulfonate (228 mg). The reaction was left to stir over night, then heated to 60C and stirred overnight. The mixture was diluted with EtOAc (20 ml.) and partitioned with water (20 imL). Two layers separated and the aqueous phase was re-extracted with EtOAc (3 x 20 imL). The organic phase was dried using a hydrophobic frit and concentrated in vacuo to give a yellow liquid. This was diluted with 10% LiCI solution and partitioned with EtOAc (20 imL). Two layers separated and the aqueous phase was bic frit and l (708 mg, nd material

Reference： [1]Patent: WO2014/140077,2014,A1 .Location in patent: Page/Page column 57-58

20
[ 161417-28-3 ]
[ 115314-14-2 ]
(R)-4-bromo-3-(oxiran-2-ylmethoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39.4 g		4-Bromopyridin-3-ol (36.9 g, 212 mmol) was taken up in DMF (667 ml.) under nitrogen. Cesium carbonate (189 g, 579 mmol) was added in one portion and the mixture stirred for 10 min. (R)- oxiran-2-ylmethyl 3-nitrobenzenesulfonate (50 g, 193 mmol) was added over -10 min and the reaction left to stir at room temperature overnight. The reaction was cooled in an ice-bath and water (1000 imL) was added slowly (exothermic). The solution was extracted with EtOAc (2 x 500 imL). The aqueous layer was diluted with brine (1000 imL) and then re-extracted with EtOAc (2 x 1000 imL). The combined organics were washed with water (2 x 2000 imL) and 5% LiCI (2000 imL) and then dried with Na2S04, filtered and concentrated in vacuo to give (R)-4-bromo-3-(oxiran-2- ylmethoxy)pyridine (39.4 g) as an orange oil. 1 H NM R (400MHz, CDCI3) delta-ppm 8.27 (1 H, s), 8.10 (1 H, d), 7.52 (1 H, d), 4.44 (1 H, dd) 4.15 (1 H, dd), 3.43 (1 H, m), 2.95 (1 H, m), 2.87 (1 H, dd). LCMS (2 min, Formic): Rt = 0.60 min, MH+ 230/232. The oil was taken up immediately into tBuOH (100 mL) for use in the next reaction.

Reference： [1]Patent: WO2014/140077,2014,A1 .Location in patent: Page/Page column 58

21
[ 161417-28-3 ]
C₁₅H₁₈N₂O₅ [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

22
[ 161417-28-3 ]
C₁₆H₂₀N₂O₇S [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

23
[ 161417-28-3 ]
C₁₉H₂₃N₅O₄ [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

24
[ 161417-28-3 ]
C₁₇H₁₉N₅O₄ [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

25
[ 161417-28-3 ]
C₁₇H₁₇N₅O₃ [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

26
[ 161417-28-3 ]
C₁₅H₁₇N₅O₄ [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

27
[ 161417-28-3 ]
C₁₅H₁₉N₃O₄ [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

28
[ 161417-28-3 ]
C₂₀H₂₂N₆O₇ [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

29
[ 161417-28-3 ]
C₁₈H₁₈N₆O₇ [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

30
[ 161417-28-3 ]
C₁₈H₂₀N₆O₅ [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

31
[ 161417-28-3 ]
C₁₈H₁₈N₆O₄ [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

32
[ 161417-28-3 ]
[ 87184-99-4 ]
C₁₅H₂₆BrNO₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 4.0h;Inert atmosphere;	Synthesis of Compound 60.1 [0428] To a solution of <strong>[161417-28-3]4-bromopyridin-3-ol</strong> (4.0 g, 23.0 mmol, 1.0 eq) and 4-((tert- butyldimethylsilyl)oxy)butan-l-ol (4.7 g, 23.0 mmol, 1.0 eq) in dry THF (60 mL), PPh3 (9.0 g, 34.5 mmol, 1.5 eq) and DIAD (9.3 g, 46.0 mmol, 2.0 eq) were added under N2 atmosphere. The resulting mixture was stirred at room temperature for 4 h and then the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (200 mL) and then washed with water (100 mL x 2). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel (PE / EA = 15 / 1) to give 60.1 (3.4 g, Y: 41%) as a colorless oil. 1H NMR (400 MHz, CDC13) delta: 8.16 (s, 1H), 7.98 (d, / = 5.2 Hz, 1H), 7.42 (d, / = 5.2 Hz, 1H), 4.11 (t, J = 6.4 Hz, 2H), 3.65 (t, J = 6.4 Hz, 2H), 1.91-1.84 (m, 2H), 1.72-1.65 (m, 2H), 0.84 (s, 9H), 0.00 (s, 6H); ESI-MS (M+H) +: 360.1.

Reference： [1]Patent: WO2014/143672,2014,A1 .Location in patent: Paragraph 0428

33
[ 161417-28-3 ]
[ 87184-99-4 ]
C₂₁H₃₂N₂O₅Si [ No CAS ]

Reference： [1]Patent: WO2014/143672,2014,A1

34
[ 161417-28-3 ]
[ 6226-25-1 ]
4-bromo-3-(2,2,2-trifluoroethoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl acetamide; at 20℃; for 1.5h;	Intermediate 1-17-1Preparation of 4-bromo-3-(2,2,2-trifluoroethoxy)pyridine300 mg (1 .72 mmol) <strong>[161417-28-3]4-bromopyridin-3-ol</strong> (CAS RN 161417-28-3) was dissolved in 7.5 mL N,N-dimethylacetamide. 310 mg (2.24 mmol) Potassium carbonate and 373 mu (2.59 mmol) 2,2,2-trifluoroethyl trifluoromethanesulfonate were added. The reaction mixture was stirred at room temperature for 90 minutes. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product was used without further purification: 400 mg (58% yield, 64% purity) of 4-bromo-3- (2,2,2-trifluoroethoxy)pyridine.1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 5.03 (q, 2H), 7.76 (d, 1 H), 8.1 1 (d, 1 H), 8.51 (s, 1 H).
	With potassium carbonate; In N,N-dimethyl acetamide; at 20℃; for 48.0h;	To a stirred solution of 4-bromopyridin-3-oI (1.00 g, 95 % purity, 5.46 mmol) in DMA (15 mL) was added potassium carbonate (981 mg, 7.10 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.2 mL, 97 % purity, 8.2 mmol). The mixture was stirred at r.t. for 48 h. Water was added (250 mL) and ammonium chloride was added until pH7 was reached. The mixture was extracted with ethyl acetate. The organic phase was washed with half-saturatedsodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum to give 1.43 g of the title compound as crude product, that was used without further purification. LC-MS (Method 2): R = 1.06 mm; MS (ESipos): m/z 256 [M+H]1H-NMR (500 MHz, DMSO-d6) a [ppm]: 4.663 (0.53), 4.682 (1.51), 4.700 (1.45), 4.718 (0.46),4.910 (0.99), 4.928 (0.93), 4.997 (4.67), 5.015 (13.93), 5.033 (13.29), 5.050 (4.20), 6.310(1.35), 6.325 (1.31), 7.739 (10.77), 7.749 (11.23), 7.845 (0.86), 7.850 (0.75), 8.156 (10.52),8.166(10.05)8.511 (16.00).

Reference： [1]Patent: WO2016/42080,2016,A1 .Location in patent: Page/Page column 149
[2]Patent: WO2017/102091,2017,A1 .Location in patent: Page/Page column 329; 330

35
[ 161417-28-3 ]
2-[1-(4-ethoxy-2,6-difluorobenzyl)-1H-indazol-3-yl]-5-methoxy-N-[3-(2,2,2-trifluoroethoxy)pyridin-4-yl]pyrimidin-4-amine [ No CAS ]

Reference： [1]Patent: WO2016/42080,2016,A1

36
[ 75-30-9 ]
[ 161417-28-3 ]
4-bromo-3-(propan-2-yloxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In N,N-dimethyl acetamide; at 70℃; for 3.0h;	To a stirred solution of <strong>[161417-28-3]4-bromopyridin-3-ol</strong> (5.00 g, 28.7 mmol) in DMA (150 mL) was added potassium carbonate (11.9 g, 86.2 mmol) and 2-iodopropane (4.3 mL, 43 mmol) and the mixture was stirred at 70C for 3 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with half-saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Aminophase-silicagelchromatography gave 4.41 g (71 % yield) of the title compound.LC-MS (Method 2): R = 1.07 mm; MS (ESIpos): m/z = 216 [M+H]1H-NMR (400 MHz, DMSO-d6) [ppm]: 1.307 (15.82), 1.311 (2.09), 1.322 (16.00), 1.326(1.88), 4.803 (0.88), 4.818 (1.18), 4.833 (0.88), 7.662 (2.23), 7.674 (2.33), 8.030 (2.72), 8.042(2.52), 8.413 (3.82).

Reference： [1]Patent: WO2017/102091,2017,A1 .Location in patent: Page/Page column 333

37
[ 161417-28-3 ]
(R)-tert-butyl 4-((7-(3-(cyclopropylmethoxy)pyridin-4-yl)-5-methyl-4-oxo-4,5-dihydrofuro[3,2-c]pyridin-2-yl)methyl)-3-methylpiperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/197056,2017,A1

38
[ 161417-28-3 ]
[ 19539-50-5 ]

Reference： [1]Patent: WO2018/71794,2018,A1

39
[ 161417-28-3 ]
[ 117103-45-4 ]

Reference： [1]Patent: WO2018/71794,2018,A1

40
[ 161417-28-3 ]
[ 193605-32-2 ]

Reference： [1]Patent: WO2018/71794,2018,A1

41
[ 161417-28-3 ]
5-chloro-2,3-dihydrofuro[2,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2018/71794,2018,A1

42
[ 161417-28-3 ]
[ 74-96-4 ]
[ 17117-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 16.0h;	To a solution of 607 <strong>[161417-28-3]4-bromopyridin-3-ol</strong> (500 mg, 2.87 mmol) in 28 DMF (10 mL) was added 608 bromoethane (313 mg, 2.87 mmol) and 54 K2CO3 (794 mg, 5.75 mmol). The mixture was heated at 60 C. for 16 hours. The mixture was concentrated. The residue was dissolved in 56 ethyl acetate (20 mL) and 99 H2O (20 mL). The organic layer was washed with H2O (20 mL×2), brine (20 mL), dried over Na2SO4, filtered and concentrated to give 609 4-bromo-3-ethoxy-pyridine.

Reference： [1]Patent: US2019/194189,2019,A1 .Location in patent: Paragraph 0738-0739

43
[ 161417-28-3 ]
3-ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine [ No CAS ]

Reference： [1]Patent: US2019/194189,2019,A1

44
[ 161417-28-3 ]
5-(3-ethoxypyridin-4-yl)-1-isopropyl-N-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[4,3-b]pyridin-7-amine [ No CAS ]

Reference： [1]Patent: US2019/194189,2019,A1

45
[ 161417-28-3 ]
5-(3-ethoxypyridin-4-yl)-1-isopropyl-3-methyl-1H-pyrazolo[4,3-b]pyridin-7-amine [ No CAS ]

Reference： [1]Patent: US2019/194189,2019,A1

46
[ 161417-28-3 ]
5-(3-ethoxy-4-pyridyl)-N-[(6-fluoro-2-pyridyl)methyl]-1-isopropyl-3-methyl-pyrazolo[4,3-b]pyridin-7-amine [ No CAS ]

Reference： [1]Patent: US2019/194189,2019,A1

47
[ 161417-28-3 ]
4-bromo-3-methoxypyridin-2-amine [ No CAS ]