[ CAS No. 934758-27-7 ] {[proInfo.proName]}

Name: 934758-27-7|2-Amino-6-bromopyridin-3-ol|95%
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SKU: A174045
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Quality Control of [ 934758-27-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 934758-27-7 ]

Product Details of [ 934758-27-7 ]

CAS No. :	934758-27-7	MDL No. :	MFCD11110242
Formula :	C₅H₅BrN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JSRWVRYNUHTJOL-UHFFFAOYSA-N
M.W :	189.01	Pubchem ID :	55264984
Synonyms :

Calculated chemistry of [ 934758-27-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	38.36
TPSA :	59.14 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) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.22
Log Po/w (XLOGP3) :	1.17
Log Po/w (WLOGP) :	1.14
Log Po/w (MLOGP) :	0.37
Log Po/w (SILICOS-IT) :	0.91
Consensus Log Po/w :	0.96

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.24
Solubility :	1.08 mg/ml ; 0.00572 mol/l
Class :	Soluble
Log S (Ali) :	-2.01
Solubility :	1.86 mg/ml ; 0.00983 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.95
Solubility :	2.15 mg/ml ; 0.0114 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.97

Safety of [ 934758-27-7 ]

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

Application In Synthesis of [ 934758-27-7 ]

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

Upstream synthesis route of [ 934758-27-7 ]
Downstream synthetic route of [ 934758-27-7 ]

[ 934758-27-7 ] Synthesis Path-Upstream 1~3

1
[ 443956-08-9 ]
[ 934758-27-7 ]

Yield	Reaction Conditions	Operation in experiment
96.55%	With iron; ammonium chloride In ethanol; water at 75℃; for 2 h;	A mixture of 6-bromo-2-nitro-pyridin-3-ol (3 g, 13.7 mmol), Fe (7657.88 mg, 136.99 mmol) and NH₄C1 (7329.1 mg, 136.99 mmol) in Ethanol (100 mL) and Water (100 mL) was stirred at 75 °C for 2 hours to give a black suspension. The reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated to give the crude product (2.5 g, 13.22 mmol, 96.55percent yield) as a solid. 1H NMR DMSO-c 400MHz δ_H = 9.71 (s, 1H), 6.74 (d, 1H), 6.50 (d, 1H), 5.92 (br s, 2H).
60%	With ammonium chloride; zinc In ethanol at 50℃; for 16 h; Inert atmosphere	Compound I-2 (1 g, 4.6 mmol) was added to a three-necked flask,Dissolved with 20 mL of ethanol,After replacing the nitrogen three times,To this was added zinc dust (1.5 g, 22.9 mmol) andAmmonium chloride (2.46 g, 46 mmol),Replace nitrogen again;50 under the conditions of reaction 16h,(CH2Cl2: CH3OH = 25: 1). The reaction solution was filtered and the filtrate was collected. After concentration under reduced pressure, the residue was purified by petroleum ether / ethyl acetate (5: 1)The grayishl solid was the target product I-3 (524 mg, 60percent).
60%	With ammonium chloride; zinc In ethanol at 50℃; for 16 h; Inert atmosphere	Under an atmosphere of nitrogen, zinc powder (1.5 g,22.9 mmol) and NH4Cl (1.5 g, 22.9 mmol) were added to the solutionof 2-nitropyridin-3-ol (17) (1 g, 4.6 mmol) in C2H5OH (20 mL).The reaction was heated to 50 C and stirred for 16 h. The crudereaction mixture was filtered and purified by flash column chromatography(PE:EA 5:1) to provide the title compound 6-bromo-2-nitropyridin-3-ol (18) (524 mg, 60percent). 1H NMR (400 MHz, DMSO)d 9.70 (s, 1H), 6.74 (d, J 7.8 Hz, 1H), 6.49 (d, J 7.8 Hz, 1H), 5.91 (s,1H); MS (M H): m/z 188.99.

57.9%

at 85℃; for 16 h;

To a stirred solution of 6-bromo-2-nitropyridin-3-ol (6 g, 27.40 mmol) in EtOH (100 mL) was added iron (11.00 g, 197.00 mmol), calcium chloride (3.04 g, 27.4 mmol) and the reaction mixture for was heated at 85 °C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through celite and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (Redisep-80 g, 10-20percent MeOH/DCM) to obtain Intermediate 115A (3.00 g, 57.90percent) as a yellow solid.¹H NMR (400 MHz, DMSO-d₆) δ ppm 6.50 (d, J = 7.78 Hz, 1 H), 6.75 (d, J = 7.78 Hz, 1 H), 9.70 (br. s, 1 H). (2 Exchangeable proton not observed). LCMS (Method-O): retention time 0.64 min, [M+2H] 191.3.

Reference： [1] Patent: WO2018/148745, 2018, A1, . Location in patent: Page/Page column 163
[2] Patent: CN107188900, 2017, A, . Location in patent: Paragraph 0039; 0042; 0043
[3] European Journal of Medicinal Chemistry, 2018, vol. 159, p. 255 - 266
[4] Patent: WO2018/93569, 2018, A1, . Location in patent: Page/Page column 198; 199
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1222 - 1237

2
[ 15128-82-2 ]
[ 934758-27-7 ]

Reference： [1] Patent: CN107188900, 2017, A,
[2] Patent: WO2018/148745, 2018, A1,
[3] European Journal of Medicinal Chemistry, 2018, vol. 159, p. 255 - 266

3
[ 934758-27-7 ]
[ 78-39-7 ]
[ 494747-09-0 ]

Reference： [1] Patent: WO2007/45622, 2007, A1, . Location in patent: Page/Page column 32

[ 934758-27-7 ] Synthesis Path-Downstream 1~64

1
[ 934758-27-7 ]
[ 78-39-7 ]
[ 494747-09-0 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; at 130℃; for 1.0h;	Example A1; 6-Bromo-2-methyl-oxazolo[4,5-b]pyridine; A solution of 20 g (106 mmol) 2-amino-6-bromo-3-hydroxy-pyridine and 0.05 g p-toluenesulfonic acid monohydrate in 22 ml triethyl orthoacetate is stirred at 13O0C for 1 h. After cooling to room temperature the reaction solution is diluted with ethyl acetate (150 ml) and extracted with water (3 x 150 ml). The combined organic phases are dried over MgSO4, filtered and concentrated in vacuo. Subsequent purification by crystallization from ethanol affords the title compound (19 g) as yellow-orange crystals. The mass spectrum shows the molecular peak MH+ at 213.2 and 215.2 Da.

Reference： [1]Patent: WO2007/45622,2007,A1 .Location in patent: Page/Page column 32

2
[ 443956-08-9 ]
[ 934758-27-7 ]

Yield	Reaction Conditions	Operation in experiment
96.55%	With iron; ammonium chloride; In ethanol; water; at 75℃; for 2h;	A mixture of 6-bromo-2-nitro-pyridin-3-ol (3 g, 13.7 mmol), Fe (7657.88 mg, 136.99 mmol) and NH4C1 (7329.1 mg, 136.99 mmol) in Ethanol (100 mL) and Water (100 mL) was stirred at 75 C for 2 hours to give a black suspension. The reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated to give the crude product (2.5 g, 13.22 mmol, 96.55% yield) as a solid. 1H NMR DMSO-c 400MHz deltaH = 9.71 (s, 1H), 6.74 (d, 1H), 6.50 (d, 1H), 5.92 (br s, 2H).
60%	With ammonium chloride; zinc; In ethanol; at 50℃; for 16h;Inert atmosphere;	Compound I-2 (1 g, 4.6 mmol) was added to a three-necked flask,Dissolved with 20 mL of ethanol,After replacing the nitrogen three times,To this was added zinc dust (1.5 g, 22.9 mmol) andAmmonium chloride (2.46 g, 46 mmol),Replace nitrogen again;50 under the conditions of reaction 16h,(CH2Cl2: CH3OH = 25: 1). The reaction solution was filtered and the filtrate was collected. After concentration under reduced pressure, the residue was purified by petroleum ether / ethyl acetate (5: 1)The grayishl solid was the target product I-3 (524 mg, 60%).
60%	With ammonium chloride; zinc; In ethanol; at 50℃; for 16h;Inert atmosphere;	Under an atmosphere of nitrogen, zinc powder (1.5 g,22.9 mmol) and NH4Cl (1.5 g, 22.9 mmol) were added to the solutionof 2-nitropyridin-3-ol (17) (1 g, 4.6 mmol) in C2H5OH (20 mL).The reaction was heated to 50 C and stirred for 16 h. The crudereaction mixture was filtered and purified by flash column chromatography(PE:EA 5:1) to provide the title compound 6-bromo-2-nitropyridin-3-ol (18) (524 mg, 60%). 1H NMR (400 MHz, DMSO)d 9.70 (s, 1H), 6.74 (d, J 7.8 Hz, 1H), 6.49 (d, J 7.8 Hz, 1H), 5.91 (s,1H); MS (M H): m/z 188.99.

57.9%

With ethanol; iron; calcium chloride; at 85℃; for 16h;

To a stirred solution of 6-bromo-2-nitropyridin-3-ol (6 g, 27.40 mmol) in EtOH (100 mL) was added iron (11.00 g, 197.00 mmol), calcium chloride (3.04 g, 27.4 mmol) and the reaction mixture for was heated at 85 C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through celite and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (Redisep-80 g, 10-20% MeOH/DCM) to obtain Intermediate 115A (3.00 g, 57.90%) as a yellow solid.1H NMR (400 MHz, DMSO-d6) delta ppm 6.50 (d, J = 7.78 Hz, 1 H), 6.75 (d, J = 7.78 Hz, 1 H), 9.70 (br. s, 1 H). (2 Exchangeable proton not observed). LCMS (Method-O): retention time 0.64 min, [M+2H] 191.3.

Reference： [1]Patent: WO2018/148745,2018,A1 .Location in patent: Page/Page column 163
[2]Patent: CN107188900,2017,A .Location in patent: Paragraph 0039; 0042; 0043
[3]European Journal of Medicinal Chemistry,2018,vol. 159,p. 255 - 266
[4]Patent: WO2018/93569,2018,A1 .Location in patent: Page/Page column 198; 199
[5]Journal of Medicinal Chemistry,2010,vol. 53,p. 1222 - 1237

3
[ 934758-27-7 ]
[ 140-89-6 ]
C₆H₃BrN₂OS [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 1222 - 1237

4
[ 934758-27-7 ]
[ 405-50-5 ]
[ 1426845-49-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	With polyphosphoric acid; at 130℃; for 4.0h;Inert atmosphere;	Step 1 - Synthesis of 5-bromo-2-(4-fluorobenzyl)oxazolo[4,5-b]pyridinePPA (2 mL) was heated at 130 C, and then 2-(4-fluorophenyl)acetic acid (400 mg, 2.6 mmol) and <strong>[934758-27-7]2-amino-6-bromopyridin-3-ol</strong> (589 mg, 3.1 mmol) were added under N2 protection. After stirred at 130 C for 4 hours, the mixture was quenched with ice and NaOH (aq). Then the mixture was extracted with EtOAc, dried over Na2S04, filtrated and concentrated. The residue was purified by column chromatography (PE : EtOAc = 15 : 1 to 10 : 1) to give the product of 5-bromo-2-(4-fluorobenzyl)oxazolo[4,5-b]pyridine (200 mg, yield: 25%). 1H-NMR (CDC13, 400 MHz) delta 7.61 (d, J= 8.4 Hz, 1H), 7.41 (d, J= 8.4 Hz, 1H), 7.34 (dd, J= 8.0, 5.6 Hz, 2H), 7.02 (t, J= 8.0 Hz, 2H), 4.28 (s, 2H). MS (M+H)+: 307 / 309.

Reference： [1]Patent: WO2013/34048,2013,A1 .Location in patent: Page/Page column 70

5
[ 934758-27-7 ]
[ 405-50-5 ]
[ 1426845-03-5 ]

Reference： [1]Patent: WO2013/34048,2013,A1

6
[ 934758-27-7 ]
C₁₇H₁₆N₂O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

7
[ 934758-27-7 ]
C₁₀H₁₀N₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

8
[ 934758-27-7 ]
6-((1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethyl)-2-oxabicyclo[2.2.2]octan-4-ylamino)methyl)-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

9
[ 934758-27-7 ]
C₁₉H₁₈N₂O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

10
[ 934758-27-7 ]
C₁₂H₁₂N₂O₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

11
[ 934758-27-7 ]
C₃₀H₃₄FN₅O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

12
[ 934758-27-7 ]
C₃₀H₃₄FN₅O₆ [ No CAS ]
C₃₀H₃₄FN₅O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

13
[ 934758-27-7 ]
C₉H₈N₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

14
[ 934758-27-7 ]
C₂₇H₃₀FN₅O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

15
[ 934758-27-7 ]
C₂₇H₃₀FN₅O₄ [ No CAS ]
C₂₇H₃₀FN₅O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

16
[ 600-00-0 ]
[ 934758-27-7 ]
[ 1196153-28-2 ]

Yield	Reaction Conditions	Operation in experiment
23%	With potassium carbonate; In acetone;Reflux;	Potassium carbonate (6.33g, 45.9mmol) Add to <strong>[934758-27-7]2-amino-6-bromo-3-hydroxypyridine</strong> (2.83 g, 9.17 mmol) And ethyl 2-bromoisobutyrate (2.7 g, 13.8 mmol) In acetone (30mL) solution, The reaction solution was heated to reflux and stirred overnight. Concentrated under reduced pressure to remove acetone. The resulting solid was dissolved in dichloromethane. Wash with water and saturated brine, respectively. The organic phase is concentrated under reduced pressure, The residue was subjected to silica gel column chromatography ( petroleum ether / ethyl acetate = 3/1) Purification afforded compound 7.1 (690 mg, yield: 23%) It is a white solid.
300 mg	With potassium carbonate; In acetone; at 20℃;Reflux;	To a suspension of <strong>[934758-27-7]2-amino-6-bromopyridin-3-ol</strong> (250 mg, 1.32 mmol) and K2CO3 in acetone (5 mL) was added ethyl 2-bromoisobutyrate (0.29 ml, 1.98 mmol) and the reaction was stirred for 1 hour at room temperature and overnight at reflux. The acetone was removed, and to the residue was added dichloromethane and water. The layers were separated and the aqueous was extracted with dichloromethane (1x). The organic layer was dried (MgSO4), filtered, and concentrated to afford 6-bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one 7.27 (300 mg).

Reference： [1]Patent: CN108623615,2018,A .Location in patent: Paragraph 0384; 0385; 0386
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643
[3]Patent: KR2016/37198,2016,A .Location in patent: Paragraph 3321-3323

17
[ 934758-27-7 ]
[ 29263-94-3 ]
C₁₁H₁₁BrN₂O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3636 - 3643

18
[ 934758-27-7 ]
6-bromo-5-cyclopropyl-3-methyloxazolo[4,5-b]pyridin-2(3H)-one [ No CAS ]

Reference： [1]Patent: US2016/145268,2016,A1

19
[ 934758-27-7 ]
5-bromo-3-methyloxazolo[4,5-b]pyridin-2(3H)-one [ No CAS ]

Reference： [1]Patent: US2016/145268,2016,A1

20
[ 934758-27-7 ]
5-cyclopropyl-3-methyloxazolo[4,5-b]pyridin-2(3H)-one [ No CAS ]

Reference： [1]Patent: US2016/145268,2016,A1

21
[ 934758-27-7 ]
[ 32315-10-9 ]
5-bromooxazolo[4,5-b]pyridin-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine; In dichloromethane; at 20℃; for 2.0h;	To an ice-cooled solution of <strong>[934758-27-7]2-amino-bromopyridinate-3-ol</strong> (15 g, 79 mmol) and triethylamine (24.33 mL, 175 mmol) in CH2Cl2 (1000 mL) was added drop-wise a solution of triphosgene (9.42 g, 31.7 mmol) in CH2Cl2 (150 mL). The resulting mixture was stirred at room temperature for 2 h, and then diluted with DCM (500 mL). The organic layer was washed water (200 mL), brine (200 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 12 g (70%) of the desired product. 1HNMR (400 MHz, CDCl3)) delta 7.55 (d, J=8.0 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 6.88 (s, 1H, D2O exchangeable); GC-MS (m/z) 214, 216 [M+, Br79, 81].

Reference： [1]Patent: US2016/145268,2016,A1 .Location in patent: Paragraph 0244

22
[ 934758-27-7 ]
C₂₅H₂₇N₅O₄*C₂HF₃O₂ [ No CAS ]

Reference： [1]Patent: KR2016/37198,2016,A

23
[ 934758-27-7 ]
[ 3832-48-2 ]
6-bromo-2,2-difluoro-4H-pyrido[3,2-b][1,4]oxazin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 50℃; for 21.0h;Cooling with ice;	A solution of <strong>[934758-27-7]2-amino-6-bromopyridin-3-ol</strong> (500 mg, 2.29 mmol) in DMF (5 mL) was treated with potassium carbonate (367.5 mg, 2.66 mmol). 2-Bromo-2,2-difluoro- acetyl chloride (566 mg, 2.93 mmol) was added dropwise over 10 minutes with cooling in an ice-water bath. The reaction mixture was warmed to room temperature over 3 h, then heated at 50C for 18 h. The resulting mixture was concentrated under reduced pressure, then EtOAc (5 mL) and water (5 mL) were added. The organic layer was separated and washed with 2M aqueous HC1 (5 mL), saturated aqueous NaHC03 solution and brine, then dried (MgSC^). The crude material was concentrated under reduced pressure. (0855) Trituration of the resulting brown oil with DCM afforded the title compound (180 mg, 26%) as an orange solid. Method B HPLC-MS: MH+ mlz 264/266, RT 1.91 minutes (100%)

Reference： [1]Patent: WO2016/198400,2016,A1 .Location in patent: Page/Page column 90

24
[ 75-15-0 ]
[ 934758-27-7 ]
5-bromooxazolo[4,5-b]pyridine-2-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In ethanol; at 80 - 85℃; for 16.0h;	Compound I-3 (0.3 g, 1.59 mmol) was added to the reaction flask,Dissolved with 10 mL of ethanol,Then, carbon disulfide (2.42 g, 31.7 mmol) was added with stirringPotassium hydroxide (191 mg, 4.76 mmol);80-85 conditions for 16h,After the TLC test reaction was complete (CH2Cl2: CH3OH = 25: 1), the ethanol and carbon disulfide were removed by concentration under reduced pressure,With dilute hydrochloric acid to adjust the system to pH 3 or so, precipitation of solid,Filtration and drying gave 0.26 g of the crude product of compound I-4,Directly to the next step.
0.26 g	With potassium hydroxide; In ethanol; at 80 - 85℃; for 16.0h;Inert atmosphere;	KOH (191 mg, 4.76 mmol) was added to a stirred mixture of 6-bromo-2-nitropyridin-3-ol (18) (0.3 g, 1.59 mmol) in C2H5OH(10 mL) under an argon atmosphere. Carbon disulfide (2.42 g,31.7 mmol) was added and the reaction mixture was heated toreflux for 16 h. The reaction mixture was evaporated to dryness,andwater (250 mL)was added followed by HCl until the pH was ~3.The formed precipitate was separated by filtration, washed with H2O, and dried to provide the crude product 19 (0.26 g).

Reference： [1]Patent: CN107188900,2017,A .Location in patent: Paragraph 0039; 0045
[2]European Journal of Medicinal Chemistry,2018,vol. 159,p. 255 - 266

25
[ 15128-82-2 ]
[ 934758-27-7 ]

Reference： [1]Patent: CN107188900,2017,A
[2]Patent: WO2018/148745,2018,A1
[3]European Journal of Medicinal Chemistry,2018,vol. 159,p. 255 - 266

26
[ 934758-27-7 ]
2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(2-fluoropyridin-3-yl)oxazolo[4,5-b]pyridine [ No CAS ]

Reference： [1]Patent: CN107188900,2017,A
[2]European Journal of Medicinal Chemistry,2018,vol. 159,p. 255 - 266

27
[ 934758-27-7 ]
2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(6-fluoropyridin-3-yl)oxazolo[4,5-b]pyridine [ No CAS ]

Reference： [1]Patent: CN107188900,2017,A
[2]European Journal of Medicinal Chemistry,2018,vol. 159,p. 255 - 266

28
[ 934758-27-7 ]
5-bromo-2-(methylthio)oxazolo[4,5-b]pyridine [ No CAS ]

Reference： [1]Patent: CN107188900,2017,A
[2]European Journal of Medicinal Chemistry,2018,vol. 159,p. 255 - 266

29
[ 934758-27-7 ]
[ 1206716-72-4 ]

Reference： [1]Patent: CN107188900,2017,A
[2]European Journal of Medicinal Chemistry,2018,vol. 159,p. 255 - 266

30
[ 934758-27-7 ]
tert-butyl (5-bromooxazolo[4,5-b]pyridin-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: US2018/65983,2018,A1
[2]Patent: US2018/65983,2018,A1

31
[ 934758-27-7 ]
methyl 2-((tert-butoxycarbonyl)amino)oxazolo[4,5-b]pyridine-5-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/65983,2018,A1
[2]Patent: US2018/65983,2018,A1
[3]Patent: US2018/65983,2018,A1
[4]Patent: US2018/65983,2018,A1

32
[ 934758-27-7 ]
2-((tert-butoxycarbonyl)amino)oxazolo[4,5-b]pyridine-5-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2018/65983,2018,A1
[2]Patent: US2018/65983,2018,A1
[3]Patent: US2018/65983,2018,A1
[4]Patent: US2018/65983,2018,A1

33
[ 934758-27-7 ]
tert-Butyl (5-((8-bromo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-6-yl)carbamoyl)oxazolo[4,5-b]pyridin-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: US2018/65983,2018,A1
[2]Patent: US2018/65983,2018,A1
[3]Patent: US2018/65983,2018,A1
[4]Patent: US2018/65983,2018,A1

34
[ 934758-27-7 ]
5-(4-bromo-8,9-dihydro-7H-6-oxa-2,9a-diazabenzo[cd]azulen-1-yl)oxazolo[4,5-b]pyridin-2-amine [ No CAS ]

Reference： [1]Patent: US2018/65983,2018,A1
[2]Patent: US2018/65983,2018,A1
[3]Patent: US2018/65983,2018,A1
[4]Patent: US2018/65983,2018,A1

35
[ 934758-27-7 ]
1-(2-aminooxazolo[4,5-b]pyridin-5-yl)-8,9-dihydro-7H-6-oxa-2,9a-diazabenzo[cd]azulen-4-ol [ No CAS ]

Reference： [1]Patent: US2018/65983,2018,A1
[2]Patent: US2018/65983,2018,A1
[3]Patent: US2018/65983,2018,A1
[4]Patent: US2018/65983,2018,A1

36
[ 934758-27-7 ]
tert-Butyl (5-(4-bromo-7,8,9,10-tetrahydro-6-oxa-2, 10a-diazacycloocta[cd]inden-1-yl)oxazolo[4,5-b]pyridin-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: US2018/65983,2018,A1
[2]Patent: US2018/65983,2018,A1
[3]Patent: US2018/65983,2018,A1
[4]Patent: US2018/65983,2018,A1

37
[ 934758-27-7 ]
[ 506-68-3 ]
5-bromooxazolo[4,5-b]pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium carbonate;	Step 1: 5-Bromooxazolo[4,5-b]pyridin-2-amine A mixture of <strong>[934758-27-7]2-amino-6-bromopyridin-3-ol</strong> (20.0 g, 105 mmol) and cyanic bromide (89.6 g, 846 mmol) in water (400 mL) was stirred at 100 C. for 20 min. The resultant mixture was quenched with sodium carbonate. The pH value of the solution was adjusted to 9 and diluted with DCM. The organic extracts were combined, dried over sodium sulfate and evaporated in vacuo. The residue was purified via flash chromatography on silica gel (solvent gradient: 0-5% methanol in DCM) to yield 10 g (44%) of the title compound as a yellow solid. LCMS (ESI): [M+H]+=214/216.

Reference： [1]Patent: US2018/65983,2018,A1

38
[ 934758-27-7 ]
5-bromo-7-(trifluoromethyl)benzo[d]oxazol-2-amine [ No CAS ]
5-bromooxazolo[4,5-b]pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		Step 1: 5-Bromooxazolo[4,5-b]pyridin-2-amine The title compound (1.45 g, 64% yield) was generated from <strong>[934758-27-7]2-amino-6-bromopyridin-3-ol</strong> (2.0 g, 10.6 mmol) following a procedure analogous to Example 235, step 1. LCMS (ESI): [M+H]+=214/216.

Reference： [1]Patent: US2018/65983,2018,A1

39
[ 1659-31-0 ]
[ 934758-27-7 ]
5-bromooxazolo[4,5-b]pyridin-2(3H)-one [ No CAS ]