[ CAS No. 53981-24-1 ] {[proInfo.proName]}

Name: 53981-24-1|2-Amino-5-fluorophenol|98%
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Quality Control of [ 53981-24-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 53981-24-1 ]

Product Details of [ 53981-24-1 ]

CAS No. :	53981-24-1	MDL No. :	MFCD00671759
Formula :	C₆H₆FNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IIDUNAVOCYMUFB-UHFFFAOYSA-N
M.W :	127.12	Pubchem ID :	185763
Synonyms :

Calculated chemistry of [ 53981-24-1 ]

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 :	32.83
TPSA :	46.25 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 :	Yes
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.03
Log Po/w (XLOGP3) :	1.07
Log Po/w (WLOGP) :	1.54
Log Po/w (MLOGP) :	1.24
Log Po/w (SILICOS-IT) :	1.09
Consensus Log Po/w :	1.19

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.8
Solubility :	2.04 mg/ml ; 0.016 mol/l
Class :	Very soluble
Log S (Ali) :	-1.63
Solubility :	2.96 mg/ml ; 0.0233 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.7
Solubility :	2.52 mg/ml ; 0.0199 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 53981-24-1 ]

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 [ 53981-24-1 ]

* 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 [ 53981-24-1 ]
Downstream synthetic route of [ 53981-24-1 ]

[ 53981-24-1 ] Synthesis Path-Upstream 1~12

1
[ 127682-43-3 ]
[ 372-20-3 ]
[ 399-95-1 ]
[ 53981-24-1 ]
[ 53981-23-0 ]

Reference： [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806

2
[ 446-36-6 ]
[ 53981-24-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogen In ethanol for 1.5 h;	Intermediate 13 2-Amino-5-fluorophenol A solution of 5-fluoro-2-nitrophenol (commercially available, for example, from Aldrich) (2.50 g, 15.9 mmol) in ethanol (50 ml) was hydrogenated over 10percent palladium on carbon (980 mg) for 1.5 h. The catalyst was removed by filtration and the filtrate was concentrated. The solid residue was taken up in ether and an equal volume of cyclohexane was added. Removal of ether in vac at room temperature afforded a pale grey solid which was filtered and washed with cyclohexane (1.90 g, 94percent). Found: C, 56.4; H, 4.8; N, 10.9. C₆H₆FNO requires C, 56.7; H, 4.8; N, 1 1.0percent.
93%	With hydrogen In ethanol	a. 2-amino-5-fluorophenol To 500 mg of 10percent palladium on carbon in a Parr bottle with 50 ml of anhydrous ethanol was added a solution of 10 g (64 mmol) 5-fluoro-2-nitrophenol in 150 ml ethanol. The flask was evacuated, charged with hydrogen and shaken on a Parr apparatus for 1 hour. The catalyst was removed by filtration through Celite.(R). and the filtrate was evaporated to dryness in vacuo to give 7.54 g (93percent yield) of a dark solid shown to be the desired product by ¹ H NMR.
93%	With hydrogen In ethanol	a. 2-amino-5-fluorophenol To 500 mg of 10percent palladium on carbon in a Parr bottle containing 50 ml of anhydrous ethanol was added a solution of 10 g (64 mmol) 5-fluoro-2-nitrophenol in 150 ml ethanol. The flask was evacuated, charged with hydrogen and shaken on a Parr apparatus for 1 hour. The catalyst was removed by filtration through. Celite.(R). and the filtrate was evaporated to dryness in vacuo to give 7.54 g (93percent yield) of a dark solid.

82%	With 10% palladium on activated carbon; Degussa type; hydrogen In methanol for 3 h;	To a of solution of 5-fluoro-2-nitrophenol (6.37 mmol, 1.00 g) in methanol (100 mL), 10percent palladium on activated carbon (10 wtpercent of 5-fluoro-2-nitrophenol, 0.10 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (15 psi) for three hours. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered over a thin pad of celite which was then washed with methanol (70 mL). The filtrate was concentrated in vacuo yielding a brown solid. Silica gel column chromatography (10:1 hexanes/chlorofrom) provided a crystalline orange solid in an 82percent yield.
44%	Stage #1: at 20℃; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	Example 62; 6-Fluoro-2-(4-(pyddin-2-yl)but-3-3Dyl)benzordloxazole ;62 (A) ;2-Amino-5-fluorophenol; A suspension of 3-fluoro-6-nitrophenol (500 mg, 3.18 mmol) and zinc (2.10 g, 31.8 mmol) in acetic acid (7.3 mL) was stirred overnight at room temperature. The reaction mixture was filtered through celite and washed with DCM. After evaporation and distillation under vacuum (2.10-2 mbar) of the solvents, the residue was dissolved in DCM. The organic phase was washed with a saturated solution of NaHC03 and brine, dried over MgS04, filtered and evaporated. The crude residue was purified by flash chromatography (DCM/MeOH 99.5: 0.5) to yield 177 mg (1.39 mmol, 44percent) of 2- amino-5-fluorophenol as an orange solid.
21.6 g	With 10% palladium on activated carbon; Degussa type; hydrogen In ethanol at 20℃; Inert atmosphere	To 5-fluoro-2-nitrophenol (26.63 g, 170 mmol) in Ethanol (250 ml) under N₂atmosphere was added palladium on carbon (10 wt percent, 250 mg, 0.235 mmol). The mixture was flushed with H₂and stirred at RT under H₂(balloon) until complete conversion according to thin layer chromatography (TLC) analysis. Pd/C was removed by filtration and the filtrate was concentrated to yield 21.6 g of the title compound. [0535] ¹H NMR (DMSO): 4.5 (br, 2H); 6.35 (dd, 1H); 6.45 (dd, 1H); 6.50 (dd, 1H); 9.5 (br, 1H).

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9742 - 9753
[2] Patent: WO2010/94643, 2010, A1, . Location in patent: Page/Page column 46
[3] Patent: US5238908, 1993, A,
[4] Patent: US5393735, 1995, A,
[5] Chemistry - A European Journal, 2011, vol. 17, # 33, p. 9076 - 9082
[6] Patent: WO2005/85202, 2005, A1, . Location in patent: Page/Page column 53
[7] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3521 - 3525
[8] Advanced Synthesis and Catalysis, 2010, vol. 352, # 11-12, p. 1834 - 1840
[9] Patent: US5886044, 1999, A,
[10] Patent: US5780483, 1998, A,
[11] Patent: US6262113, 2001, B1,
[12] Patent: WO2005/123703, 2005, A2, . Location in patent: Page/Page column 121-122
[13] Collection of Czechoslovak Chemical Communications, 1994, vol. 59, # 9, p. 2119 - 2122
[14] Patent: US6136831, 2000, A,
[15] Patent: EP2172453, 2010, A1, . Location in patent: Page/Page column 14-15
[16] Patent: WO2010/145992, 2010, A1, . Location in patent: Page/Page column 87; 88
[17] Patent: WO2011/57935, 2011, A1, . Location in patent: Page/Page column 67
[18] Patent: WO2012/41789, 2012, A1, . Location in patent: Page/Page column 77
[19] Patent: WO2012/80239, 2012, A1, . Location in patent: Page/Page column 69
[20] Patent: US2013/267417, 2013, A1, . Location in patent: Paragraph 0533-0535
[21] Journal of Materials Chemistry A, 2017, vol. 5, # 22, p. 10986 - 10997
[22] Archiv der Pharmazie, 2018, vol. 351, # 5,

3
[ 367-25-9 ]
[ 53981-24-1 ]

Reference： [1] Patent: CN107459495, 2017, A, . Location in patent: Paragraph 0036; 0037; 0044; 0045

4
[ 127682-43-3 ]
[ 372-20-3 ]
[ 399-95-1 ]
[ 53981-24-1 ]
[ 53981-23-0 ]

Reference： [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806

5
[ 127682-43-3 ]
[ 372-20-3 ]
[ 399-95-1 ]
[ 53981-24-1 ]
[ 53981-23-0 ]

Reference： [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806

6
[ 3054-95-3 ]
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[ 135838-04-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With hydrogenchloride In water at 111℃; for 24 h;	General procedure: A 1N HCl solution (82.5 mL) was added to the aniline (~1 mmol) in a round bottom flask. To this was added acrolein diethyl acetal (2.5 mmol). The resulting solution was refluxed at 111 °C for 24 hours. After cooling to room temperature, the solution was neutralized (pH 7−8) by addition of solid Na2CO3. The product was then extracted into dichloromethane (3 x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was then purified by column chromatography (elution mixture of hexane with ethyl acetate or 15percent ethyl acetate/cyclohexane with methanol) to give the desired quinoline product.

Reference： [1] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6436 - 6439

7
[ 53981-24-1 ]
[ 107-02-8 ]
[ 135838-04-9 ]

Yield	Reaction Conditions	Operation in experiment
12%	Stage #1: With hydrogenchloride In water; toluene at 100℃; Stage #2: With sodium hydroxide In water	Intermediate 14 6-Fluoro-8-q uinolinol 2-Amino-5-fluorophenol (for example, as prepared for Intermediate 13) (602 mg, 4.74 mmol) was dissolved in 5M hydrochloric acid (21 ml). Toluene (6.5 ml) and acrolein (1 ml, 14 mmol) were added to the solution and the mixture was stirred at 100⁰C overnight. The aqueous layer was removed and 10M sodium hydroxide was added until the solution was neutral. The compound which precipitated was extracted with dichloromethane and the organic phase was washed with water and brine, then it was dried with sodium sulphate, filtered and evaporated. The residue was dissolved in dichloromethane and purified by Flashmaster (50 g cartridge, 0-50percent ethyl acetate- dichloromethane, 60 min). Pure fractions were combined and evaporated to give the title compound (96 mg, 12percent). LCMS RT=1.97 min, ES+ve m/z 164 (M+H)⁺. RT=2.85 min, ES+ve m/z 176 (M+H)⁺.

Reference： [1] Chemical Communications, 2015, vol. 51, # 84, p. 15458 - 15461
[2] Patent: WO2010/94643, 2010, A1, . Location in patent: Page/Page column 46

8
[ 53981-24-1 ]
[ 56-81-5 ]
[ 135838-04-9 ]

Reference： [1] Monatshefte fur Chemie, 2002, vol. 133, # 11, p. 1437 - 1442

9
[ 53981-24-1 ]
[ 153403-53-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 16, p. 4689 - 4693
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1975 - 1980
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
[4] Patent: WO2014/164749, 2014, A1,

10
[ 53981-24-1 ]
[ 79-04-9 ]
[ 103361-99-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tetra-N-butylammonium tribromide; potassium carbonate In acetonitrileReflux	To a suspension of 2-amino-5-fluorophenol (Alfa, 15.00 g, 118 mmol), K₂CO₃(48.9 g, 354 mmol) and tetrabutyl-ammonium bromide (3.80 g, 11.80 mmol) in MeCN (200 mL) was added 2-chloroacetyl chloride (14.66 g, 130 mmol) dropwise at 0° C. The reaction mixture was warmed to rt and then heated at reflux overnight. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The solid was collected, washed with water (100 mL) and dried in vacuo to give 7-fluoro-4H-benzo[1,4]oxazin-3-one as a pale solid (17.2 g, 87percent). ¹H NMR (DMSO-d₆, 400 MHz): δ10.71 (s, 1H), 6.84-6.88 (m, 2H), 6.76-6.81 (m, 1H), 4.57 (s, 2H).

Reference： [1] Archiv der Pharmazie, 2018, vol. 351, # 5,
[2] Patent: US2014/206663, 2014, A1, . Location in patent: Paragraph 0977; 0978
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 1, p. 222 - 236
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4700 - 4704

11
[ 53981-24-1 ]
[ 96-34-4 ]
[ 103361-99-5 ]

Reference： [1] Patent: CN107459495, 2017, A, . Location in patent: Paragraph 0036; 0038; 0048; 0049

12
[ 53981-24-1 ]
[ 103361-99-5 ]

Reference： [1] Patent: WO2014/78802, 2014, A1,

[ 53981-24-1 ] Synthesis Path-Downstream 1~28

1
[ 127682-43-3 ]
[ 372-20-3 ]
[ 399-95-1 ]
[ 53981-24-1 ]
[ 53981-23-0 ]

Reference： [1]Journal of the American Chemical Society,1992,vol. 114,p. 9795 - 9806

2
[ 446-36-6 ]
[ 53981-24-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With ammonium formate; palladium(II) hydroxide In methanol for 0.166667h; Inert atmosphere;	140 Preparation 140: 2-amino-5-fluorophenol To a solution of 5-fluoro-2-nitrophenol (2 g, 12.73 mmol) and ammonium formate (4.01 g, 63.65 mmol) in methanol (20 mL), 20% Pd(OH)2 (0.91 g, 1.27 mmol) was added under nitrogen. Immediately after addition of 20% Pd(OH)2 the temperature of the solution increased and strong bubbling was observed for a few minutes. After 10 minutes the solution was filtered and evaporated under reduced pressure to get 2-amino-5- fluorophenol (p140, 1 .7 g, y= quant) as a yellow oil. MS (mlz): 128.2 [MH]+
96%	With palladium 10% on activated carbon; hydrogen In methanol for 10h;
94%	With hydrogen In ethanol for 1.5h;	13 Intermediate 13 2-Amino-5-fluorophenol A solution of 5-fluoro-2-nitrophenol (commercially available, for example, from Aldrich) (2.50 g, 15.9 mmol) in ethanol (50 ml) was hydrogenated over 10% palladium on carbon (980 mg) for 1.5 h. The catalyst was removed by filtration and the filtrate was concentrated. The solid residue was taken up in ether and an equal volume of cyclohexane was added. Removal of ether in vac at room temperature afforded a pale grey solid which was filtered and washed with cyclohexane (1.90 g, 94%). Found: C, 56.4; H, 4.8; N, 10.9. C6H6FNO requires C, 56.7; H, 4.8; N, 1 1.0%.

93%	With hydrogen In ethanol	18.a a. a. 2-amino-5-fluorophenol To 500 mg of 10% palladium on carbon in a Parr bottle with 50 ml of anhydrous ethanol was added a solution of 10 g (64 mmol) 5-fluoro-2-nitrophenol in 150 ml ethanol. The flask was evacuated, charged with hydrogen and shaken on a Parr apparatus for 1 hour. The catalyst was removed by filtration through Celite and the filtrate was evaporated to dryness in vacuo to give 7.54 g (93% yield) of a dark solid shown to be the desired product by 1 H NMR.
93%	With hydrogen In ethanol	31.a a. a. 2-amino-5-fluorophenol To 500 mg of 10% palladium on carbon in a Parr bottle containing 50 ml of anhydrous ethanol was added a solution of 10 g (64 mmol) 5-fluoro-2-nitrophenol in 150 ml ethanol. The flask was evacuated, charged with hydrogen and shaken on a Parr apparatus for 1 hour. The catalyst was removed by filtration through. Celite and the filtrate was evaporated to dryness in vacuo to give 7.54 g (93% yield) of a dark solid.
91%	With tin(ll) chloride In ethanol for 10h; Reflux;
86%	With hydrogen In tetrahydrofuran at 20℃; for 1h;
82%	With palladium 10% on activated carbon; hydrogen In methanol for 3h;	2-amino-5-fluorophenol (KR-200F) To a of solution of 5-fluoro-2-nitrophenol (6.37 mmol, 1.00 g) in methanol (100 mL), 10% palladium on activated carbon (10 wt% of 5-fluoro-2-nitrophenol, 0.10 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (15 psi) for three hours. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered over a thin pad of celite which was then washed with methanol (70 mL). The filtrate was concentrated in vacuo yielding a brown solid. Silica gel column chromatography (10:1 hexanes/chlorofrom) provided a crystalline orange solid in an 82% yield.
79%	With cobalt(II) phthalocyanine; hydrazine hydrate In ethylene glycol at 120℃; for 4.5h; chemoselective reaction;
77%		48 a)Synthesis of 2-hydroxy 4-fluoro aniline a)Synthesis of 2-hydroxy 4-fluoro aniline 3-fluoro 6-nitro phenol (2 g, 11 mmol) was treated with 10% Pd/C(1 g) at 23° C. The reaction mixture was flushed with hydrogen gas and the reaction was allowed to stir 12 h before it was filtered through celite. The filtrate was concentrated in vacuo to afford the title compound (1.4 g, 77%). EI-MS m/z 169(M+H)+
77%		48 a)Synthesis of 2-hydroxy 4-fluoro aniline a)Synthesis of 2-hydroxy 4-fluoro aniline 3-fluoro 6-nitro phenol (2 g, 11 mmol) was treated with 10%Pd/C(1 g) at 23° C. The reaction mixture was flushed with hydrogen gas and the reaction was allowed to stir 12 h before it was filtered through celite. The filtrate was concentrated in vacuo to afford the title compound (1.4 g, 77%). EI-MS m/z 169(M+H)+
77%		48.a a) a) Synthesis of 2-hydroxy 4-fluoro aniline 3-fluoro 6-nitro phenol (2 g, 11 mmol) was treated with 10%Pd/C (1 g) at 23° C. The reaction mixture was flushed with hydrogen gas and the reaction was allowed to stir 12 h before it was filtered through celite. The filtrate was concentrated in vacuo to afford the title compound (1.4 g, 77%). EI-MS m/z 169 (M+H)+
44%	Stage #1: 5-fluoro-2-nitrophenol With acetic acid; zinc at 20℃; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	62.62(A) Example 62; 6-Fluoro-2-(4-(pyddin-2-yl)but-3-3Dyl)benzordloxazole ;62 (A) ;2-Amino-5-fluorophenol; A suspension of 3-fluoro-6-nitrophenol (500 mg, 3.18 mmol) and zinc (2.10 g, 31.8 mmol) in acetic acid (7.3 mL) was stirred overnight at room temperature. The reaction mixture was filtered through celite and washed with DCM. After evaporation and distillation under vacuum (2.10-2 mbar) of the solvents, the residue was dissolved in DCM. The organic phase was washed with a saturated solution of NaHC03 and brine, dried over MgS04, filtered and evaporated. The crude residue was purified by flash chromatography (DCM/MeOH 99.5: 0.5) to yield 177 mg (1.39 mmol, 44%) of 2- amino-5-fluorophenol as an orange solid.
	With hydrogen In ethanol
	In ethanol	R.1.i (4) i) To 50 ml of ethanol was added 5-fluoro-2-nitrophenol (7.86 g, 50 mmol) and 10% Pd/C (0.786 g) and the mixture was stirred under a hydrogen stream for 3 hours at room temperature. Then the reaction mixture was filtered and the filtrate concentrated. The residue was subjected to recrystallization from toluene to afford 2-amino-5-fluoro-phenol (5.52 g, yield: 87%). NMR(DMSO-d6 -D2 O) δ: 6.38 (1H, dt, J=3.0 Hz, 8.6 Hz), 6.49 (1H, dd, J=3.0 Hz, 10.5 Hz), 6.56 (1H, dd, J=5.3 Hz, 8.6 Hz)
	With hydrogen In methanol at 20℃;	19 Synthesis of 7-fluoro-3,4-dihydro-2H-1,4-benzoxazine To a solution of 5-fluoro-2-nitrophenol (9.50 g) in methanol (10 ml), 5% palladium on activated carbon (1.90 g) was added and stirred overnight under a hydrogen atmosphere at room temperature. The catalyst was filtered off and the solvent was distilled off under reduced pressure. The resulting residue was converted into a powder form by addition of chloroform, and then collected by filtration to give 2-amino-5-fluorophenol (6.81 g) as a brown powder. To a solution of 2-amino-5-fluorophenol thus obtained (3.00 g) in N,N-dimethylformamide (20 ml), potassium carbonate (16.31 g) and 1,2-dibromoethane (3.05 ml) were added and stirred at 125°C for 10 hours. The reaction mixture was allowed to stand overnight at room temperature, to which additional 1,2-dibromoethane (1.52 ml) was then added and stirred at 125°C for 7 hours. After cooling at room temperature, the reaction mixture was diluted with water under ice cooling and extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, dried over anhydrous sodium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure. The resulting residue was purified by NH silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate = 9:1 to 7:3) to give the titled compound, i.e., 7-fluoro-3,4-dihydro-2H-1,4-benzoxazine (1.15 g) as a red-brown oil. 1H NMR (300 MHz, CHLOROFORM-D) δ 3.35-3.42 (m, 2 H), 3.60 (brs, 1 H), 4.22-4.26 (m, 2 H), 6.44-6.56 (m, 3 H).
	With hydrogen In ethanol at 20℃; Inert atmosphere;	4.1 Example 1 : 1 ,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H- benzo[b][1 ,4]oxazin-6-yl)-1 ,3,5-triazinane-2,4-dione 4.1 : 2-amino-5-fluorophenol To 5-fluoro-2-nitrophenol (26.63 g, 170 mmol) in Ethanol (250 ml) under N2 atmosphere was added palladium on carbon (10 wt%, 250 mg, 0.235 mmol). The mixture was flushed with H2 and stirred at RT under H2 (balloon) until complete conversion according to thin layer chromatography (TLC) analysis. Pd/C was removed by filtration and the filtrate was concentrated to yield 21.6 g of the title compound. 1H NMR(DMSO): 4.5 (br, 2H); 6.35 (dd, 1 H); 6.45 (dd, 1 H); 6.50 (dd, 1 H); 9.5 (br, 1 H).
	With hydrogen In ethanol at 20℃; Inert atmosphere;	1.1 To 5-fluoro-2-nitrophenol (26.63 g, 170 mmol) in ethanol under N2 atmosphere was added palladium on carbon (10 wt%, 250 mg, 0.235 mmol). The mixture was flushed with H2 and stirred at RT under H2 (balloon) until complete conversion according to thin layer chromatography (TLC) analysis. Pd/C was removed by filtration and the filtrate was concentrated to yield 21.6 g of the title compound.H NMR(DMSO): 4.5 (br, 2H), 6.35 (dd, 1 H), 6.45 (dd, 1 H), 6.50 (dd, 1 H), 9.5 (br, 1 H).
	With hydrogen In ethanol at 20℃; Inert atmosphere;	1.1 To 5-fluoro-2-nitrophenol (26.63 g, 170 mmol) in ethanol under N2 atmosphere was added palladium on carbon (10 wt%, 250 mg, 0.235 mmol). The mixture was flushed with H2 and stirred at RT under H2 (balloon) until complete conversion according to thin layer chromatography (TLC) analysis. Pd/C was removed by filtration and the filtrate was concentrated to yield 21 .6 g of the title compound.1H NMR(DMSO): 4.5 (br, 2H), 6.35 (dd, 1 H), 6.45 (dd, 1 H), 6.50 (dd, 1 H), 9.5 (br, 1 H).
	With hydrogen In ethanol at 20℃; Inert atmosphere;	1.4.1 To 5-fluoro-2-nitrophenol (26.63 g, 170 mmol) in Ethanol (250 ml) under N2 atmosphere was added palladium on carbon (10 wt%, 250 mg, 0.235 mmol). The mixture was flushed with H2 and stirred at RT under H2 (balloon) until complete conversion according to thin layer chromatography (TLC) analysis. Pd/C was removed by filtration and the filtrate was concentrated to yield 21 .6 g of the title compound.1H NMR(DMSO): 4.5 (br, 2H); 6.35 (dd, 1 H); 6.45 (dd, 1 H); 6.50 (dd, 1 H); 9.5 (br, 1 H).
21.6 g	With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; Inert atmosphere;	1.4.1 2-amino-5-fluorophenol To 5-fluoro-2-nitrophenol (26.63 g, 170 mmol) in Ethanol (250 ml) under N2 atmosphere was added palladium on carbon (10 wt %, 250 mg, 0.235 mmol). The mixture was flushed with H2 and stirred at RT under H2 (balloon) until complete conversion according to thin layer chromatography (TLC) analysis. Pd/C was removed by filtration and the filtrate was concentrated to yield 21.6 g of the title compound. [0535] 1H NMR (DMSO): 4.5 (br, 2H); 6.35 (dd, 1H); 6.45 (dd, 1H); 6.50 (dd, 1H); 9.5 (br, 1H).
	With sodium tetrahydroborate In water at 25℃; Green chemistry;
	With iron; acetic acid In ethanol; water
	With palladium on activated charcoal; hydrogen In ethanol at 20℃;
	With sodium tetrahydroborate; water
	With iron; acetic acid In ethanol; water at 60℃;

Reference： [1]Current Patent Assignee: CHRONOS THERAPEUTICS LIMITED - WO2019/43407, 2019, A1 Location in patent: Page/Page column 131
[2]Janssen, Freek J.; Baggelaar, Marc P.; Hummel, Jessica J. A.; Overkleeft, Herman S.; Cravatt, Benjamin F.; Boger, Dale L.; Van Der Stelt, Mario [Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9742 - 9753]
[3]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2010/94643, 2010, A1 Location in patent: Page/Page column 46
[4]Current Patent Assignee: DOW INC - US5238908, 1993, A
[5]Current Patent Assignee: CORTEVA INC - US5393735, 1995, A
[6]Perez-Bolivar, Cesar; Takizawa, Shin-Ya; Nishimura, Go; Montes, Victor A.; Anzenbacher, Pavel [Chemistry - A European Journal, 2011, vol. 17, # 33, p. 9076 - 9082]
[7]Current Patent Assignee: MERCK KGAA - WO2005/85202, 2005, A1 Location in patent: Page/Page column 53
[8]Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3521 - 3525]
[9]Location in patent: experimental part Sharma, Upendra; Kumar, Praveen; Kumar, Neeraj; Kumar, Vishal; Singh, Bikram [Advanced Synthesis and Catalysis, 2010, vol. 352, # 11-12, p. 1834 - 1840]
[10]Current Patent Assignee: GLAXOSMITHKLINE PLC - US5886044, 1999, A
[11]Current Patent Assignee: GLAXOSMITHKLINE PLC - US5780483, 1998, A
[12]Current Patent Assignee: GLAXOSMITHKLINE PLC - US6262113, 2001, B1
[13]Current Patent Assignee: ADDEX THERAPEUTICS SA - WO2005/123703, 2005, A2 Location in patent: Page/Page column 121-122
[14]Radl, Stanislav [Collection of Czechoslovak Chemical Communications, 1994, vol. 59, # 9, p. 2119 - 2122]
[15]Current Patent Assignee: ASKA PHARMACEUTICAL CO., LTD. - US6136831, 2000, A
[16]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD. - EP2172453, 2010, A1 Location in patent: Page/Page column 14-15
[17]Current Patent Assignee: BASF SE - WO2010/145992, 2010, A1 Location in patent: Page/Page column 87; 88
[18]Current Patent Assignee: BASF SE - WO2011/57935, 2011, A1 Location in patent: Page/Page column 67
[19]Current Patent Assignee: BASF SE - WO2012/41789, 2012, A1 Location in patent: Page/Page column 77
[20]Current Patent Assignee: BASF SE - WO2012/80239, 2012, A1 Location in patent: Page/Page column 69
[21]Current Patent Assignee: BASF SE - US2013/267417, 2013, A1 Location in patent: Paragraph 0533-0535
[22]Zhang, Xiaofei; Chen, Lixin; Yun, Jin; Wang, Xiaodong; Kong, Jie [Journal of Materials Chemistry A, 2017, vol. 5, # 22, p. 10986 - 10997]
[23]Méndez-Rojas, Claudio; Quiroz, Gabriel; Faúndez, Mario; Gallardo-Garrido, Carlos; Pessoa-Mahana, C. David; Chung, Hery; Gallardo-Toledo, Eduardo; Saitz-Barría, Claudio; Araya-Maturana, Ramiro; Kogan, Marcelo J.; Zúñiga-López, María C.; Iturriaga-Vásquez, Patricio; Valenzuela-Gutiérrez, Carla; Pessoa-Mahana, Hernán [Archiv der Pharmazie, 2018, vol. 351, # 5]
[24]Aitken, Laura; Benek, Ondrej; Chribek, Matej; Dolezal, Rafael; Gunn-Moore, Frank; Hrabinova, Martina; Hroch, Lukas; Jun, Daniel; Kralova, Vendula; Kuca, Kamil; Lycka, Antonin; Musilek, Kamil; Prchal, Lukas; Schmidt, Monika; Vinklarova, Lucie; Zemanova, Lucie [International Journal of Molecular Sciences, 2020, vol. 21, # 6]
[25]Yang, Dong; Liu, Pei; Lin, Wanran; Sui, Shanglin; Huang, Long-Biao; Xu, Ben Bin; Kong, Jie [Chemistry - An Asian Journal, 2020, vol. 15, # 16, p. 2499 - 2504]
[26]Alarcón-Espósito, Jazmín; Araya-Maturana, Ramiro; Cabezas, David; Cerda-Cavieres, Christopher; Chung, Hery; Iturriaga-Vásquez, Patricio; Mella-Raipán, Jaime; Ojeda-Gómez, Claudia; Pessoa-Mahana, Carlos D.; Pessoa-Mahana, Hernán; Quiroz, Gabriel; Reyes-Parada, Miguel; Rodríguez-Lavado, Julio; Saitz, Claudio [Molecules, 2020, vol. 25, # 20]

3
[ 53981-24-1 ]
[ 56-81-5 ]
[ 135838-04-9 ]

Reference： [1]Monatshefte fur Chemie,2002,vol. 133,p. 1437 - 1442

4
[ 53981-24-1 ]
[ 153403-53-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4689 - 4693
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1975 - 1980
[3]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3044 - 3049
[4]Patent: WO2014/164749,2014,A1

5
[ 75-44-5 ]
[ 53981-24-1 ]
[ 2923-94-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate In dichloromethane; toluene	18.b b. b. 6-fluoro-1,3-benzoxazolin-2(3H)-one To 5.0 g (39.3 mmol) 2-amino-5-fluorophenol in 150 ml of CH2 Cl2 at 0° C. was added 13.4 (98 mmol) of potassium carbonate and 23 g (47 mmol) of 20 wt % phosgene in toluene. After warming to room temperature, the reaction was stirred an additional hour before pouring into 200 ml ice/water. The layers were separated and the aqueous phase was extracted with EtOAc (1*100 ml) before the organics were combined and dried over Na2 SO4. The solvent was removed in vacuo to give 5.76 g (96% yield) of the desired product as determined by 1 H NMR.
96%	With potassium carbonate In dichloromethane; toluene	31.b b. b. 6-fluoro-1,3-benzoxazolin-2(3H)-one To 5.0 g (39.3 mmol) 2-amino-5-fluorophenol in 150 ml of CH2 Cl2 at 0° C. was added 13.4 (98 mmol) of potassium carbonate and 23 g (47 mmol) of 20 wt. % phosgene in toluene. After warming to room temperature, the reaction was stirred an additional hour before quenching onto 200 ml ice/water. The layers were separated and the aqueous phase was extracted with EtOAc (1*100 ml) before the organics were combined and dried over Na2 SO4. The solvent was removed in vacuo to give 5.76 g (96% yield) of the desired product as determined by 1 H NMR.

Reference： [1]Current Patent Assignee: DOW INC - US5238908, 1993, A
[2]Current Patent Assignee: CORTEVA INC - US5393735, 1995, A

6
[ 53981-24-1 ]
[ 79-04-9 ]
[ 103361-99-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tetra-N-butylammonium tribromide; potassium carbonate; In acetonitrile;Reflux;	To a suspension of 2-amino-5-fluorophenol (Alfa, 15.00 g, 118 mmol), K2CO3 (48.9 g, 354 mmol) and tetrabutyl-ammonium bromide (3.80 g, 11.80 mmol) in MeCN (200 mL) was added 2-chloroacetyl chloride (14.66 g, 130 mmol) dropwise at 0 C. The reaction mixture was warmed to rt and then heated at reflux overnight. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The solid was collected, washed with water (100 mL) and dried in vacuo to give 7-fluoro-4H-benzo[1,4]oxazin-3-one as a pale solid (17.2 g, 87%). 1H NMR (DMSO-d6, 400 MHz): delta10.71 (s, 1H), 6.84-6.88 (m, 2H), 6.76-6.81 (m, 1H), 4.57 (s, 2H).
76.05%	With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; at 65℃; for 15h;Inert atmosphere;	To 2-amino-5-fluorophenol (500mg, 3.94mmol)Acetonitrile (5mL)Chloroacetyl chloride (490mg, 4.33mmol),Potassium carbonate (1.63g, 11.82mmol)And tetrabutylammonium bromide (126 mg, 0.39 mmol).The reaction mixture was heated to 65 C under a nitrogen atmosphere for 15 hours.Cool to room temperature, suction filter, and concentrate the filtrate in vacuo.Purification by column chromatography gave the compound as a yellow oil (500 mg, yield: 76.05%).

Reference： [1]Archiv der Pharmazie,2018,vol. 351
[2]Patent: US2014/206663,2014,A1 .Location in patent: Paragraph 0977; 0978
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 222 - 236
[4]Patent: CN110511220,2019,A .Location in patent: Paragraph 0496-0500
[5]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4700 - 4704

7
[ 5424-01-1 ]
[ 53981-24-1 ]
[ 1146950-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In ethyl acetate; N,N-dimethyl-formamide	50 2-[3-[5-amino-6-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-yl]phenyl]acetic acid 3-Aminopyrazine-2-carboxylic acid (5 g) and 2-amino-5-fluorophenol (5.9 g) were dissolved into DMF (30 ml). Triethylamine (5.8 g) and HATU (19.2 g) were added to the mixture. The resulting mixture was stirred at room temperature for 24 hours. Ethyl acetate (100 ml) was added to the mixture. The resulting mixture was washed with brine (20 ml*3). The organic phase was dried and concentrated. The resulting residue was purified by chromatography on silica gel to give 3-amino-N-(4-fluoro-2-hydroxyphenyl)pyrazine-2-carboxamide (6 g). NMR Spectrum: (DMSOd6, 400 MHz) 6.60 (m, 2H), 7.50 (br s, 2H), 7.80 (s, 1H), 8.30 (m, 2H), 10.2 (s, 1H), 10.8 (s, 1H); Mass spectrum: MH+ 249.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2009/118305, 2009, A1

8
[ 53981-24-1 ]
[ 106-93-4 ]
[ 56346-41-9 ]

Yield	Reaction Conditions	Operation in experiment
43%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 6h;	A suspension of 2-amino-5-fluorophenol (5.0 g, 39.37 mmol), 1,2-dibromoethane (21.9 g, 118.15 mmol), and potassium carbonate (27.16 g, 196.8 mmol) in DMF (50 mL) was stirred at 100C for 6 h. The reaction was diluted with water and extracted the product into ethyl acetate. The combined organic layer was washed with water, brine, dried over anhyd. Na2S04 and concentrated in vacuo. The residue was purified by column chromatography over silica gel (100-200 mesh) with 10% ethyl acetate in pet-ether as eluant gave 2.6 g (43%) of 7-fluoro-3,4- dihydro-2H-benzo[b][1,4]oxazine I-73 as a brown solid. 1H NMR (400 MHz, CDCI3): 6.46-6.55 (m, 3H), 4.24 (t, J = 4.4 Hz, 2H), 3.61 (br. s, 1H), 3.38 (t, J = 4.4 Hz, 2H).
	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 125℃;	To a solution of 5-fluoro-2-nitrophenol (9.50 g) in methanol (10 ml), 5% palladium on activated carbon (1.90 g) was added and stirred overnight under a hydrogen atmosphere at room temperature. The catalyst was filtered off and the solvent was distilled off under reduced pressure. The resulting residue was converted into a powder form by addition of chloroform, and then collected by filtration to give 2-amino-5-fluorophenol (6.81 g) as a brown powder. To a solution of 2-amino-5-fluorophenol thus obtained (3.00 g) in N,N-dimethylformamide (20 ml), potassium carbonate (16.31 g) and 1,2-dibromoethane (3.05 ml) were added and stirred at 125C for 10 hours. The reaction mixture was allowed to stand overnight at room temperature, to which additional 1,2-dibromoethane (1.52 ml) was then added and stirred at 125C for 7 hours. After cooling at room temperature, the reaction mixture was diluted with water under ice cooling and extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, dried over anhydrous sodium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure. The resulting residue was purified by NH silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate = 9:1 to 7:3) to give the titled compound, i.e., 7-fluoro-3,4-dihydro-2H-1,4-benzoxazine (1.15 g) as a red-brown oil. 1H NMR (300 MHz, CHLOROFORM-D) δ 3.35-3.42 (m, 2 H), 3.60 (brs, 1 H), 4.22-4.26 (m, 2 H), 6.44-6.56 (m, 3 H).

Reference： [1]Patent: WO2014/78813,2014,A1 .Location in patent: Page/Page column 143; 144
[2]Patent: EP2172453,2010,A1 .Location in patent: Page/Page column 14-15

9
[ 53981-24-1 ]
[ 107-02-8 ]
[ 135838-04-9 ]

Yield	Reaction Conditions	Operation in experiment
12%		Intermediate 14 6-Fluoro-8-q uinolinol 2-Amino-5-fluorophenol (for example, as prepared for Intermediate 13) (602 mg, 4.74 mmol) was dissolved in 5M hydrochloric acid (21 ml). Toluene (6.5 ml) and acrolein (1 ml, 14 mmol) were added to the solution and the mixture was stirred at 1000C overnight. The aqueous layer was removed and 10M sodium hydroxide was added until the solution was neutral. The compound which precipitated was extracted with dichloromethane and the organic phase was washed with water and brine, then it was dried with sodium sulphate, filtered and evaporated. The residue was dissolved in dichloromethane and purified by Flashmaster (50 g cartridge, 0-50% ethyl acetate- dichloromethane, 60 min). Pure fractions were combined and evaporated to give the title compound (96 mg, 12%). LCMS RT=1.97 min, ES+ve m/z 164 (M+H)+. RT=2.85 min, ES+ve m/z 176 (M+H)+.

Reference： [1]Chemical Communications,2015,vol. 51,p. 15458 - 15461
[2]Patent: WO2010/94643,2010,A1 .Location in patent: Page/Page column 46

10
[ 53981-24-1 ]
[ 7693-46-1 ]
[ 2923-94-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 20℃; for 1h;

Reference： [1]Location in patent: scheme or table Hare, Alissa A.; Leng, Lin; Gandavadi, Sunilkumar; Du, Xin; Cournia, Zoe; Bucala, Richard; Jorgensen, William L. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5811 - 5814]

11
[ 683-98-7 ]
[ 53981-24-1 ]
[ 1258836-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl bromodifluoroacetate; 2-amino-5-fluorophenol With sodium hydride In tetrahydrofuran; mineral oil at -15 - 0℃; Stage #2: With ammonium chloride In tetrahydrofuran; water; mineral oil	4.2.b Alternative b) To 2-amino-5-fluorophenol (200 mg, 1.573 mmol) in dry Tetrahydrofuran at 0 0C was added sodium hydride (55 wt% in mineral oil, 68.6 mg, 1.573 mmol). The resulting mixture was stirred for 15 minutes at -15 0C. Subsequently methyl 2-bromo-2,2- difluoroacetate (327 mg, 1.731 mmol) was added dropwise and the resulting mixture was stirred at 0 0C for two hours. The reaction mixture was quenched in saturated aqueous NH4CI solution and extracted with ethyl acetate. The combined extracts were washed with brine, dried with Na2SU4 and concentrated to yield 450 mg of the title compound1H NMR(DMSO): 3.3 (br, 1 H); 6.8 (m, 2H); 7.25 (dd, 1 H); 10.4 (br, 1 H).
	Stage #1: 2-amino-5-fluorophenol With sodium hydride In tetrahydrofuran; mineral oil at -15 - 0℃; for 0.25h; Stage #2: methyl bromodifluoroacetate In tetrahydrofuran; mineral oil at 0℃; for 2h;	1.2.b To 2-amino-5-fluorophenol (200 mg, 1 .573 mmol) in dry tetrahydrofuran at 0 °C was added sodium hydride (55 wt% in mineral oil, 68.6 mg, 1 .573 mmol). The resulting mixture was stirred for 15 minutes at -15 °C. Subsequently methyl 2-bromo-2,2- difluoroacetate (327 mg, 1 .731 mmol) was added dropwise and the resulting mixture was stirred at 0 °C for two hours. The reaction mixture was quenched in saturated aqueous NH4CI solution and extracted with ethyl acetate. The combined extracts were washed with brine, dried with Na2S04 and concentrated to yield 450 mg of the title compoundH NMR (DMSO): 3.3 (br, 1 H), 6.8 (m, 2H), 7.25 (dd, 1 H), 10.4 (br, 1 H).

Reference： [1]Current Patent Assignee: BASF SE - WO2010/145992, 2010, A1 Location in patent: Page/Page column 88; 89
[2]Current Patent Assignee: BASF SE - WO2011/57935, 2011, A1 Location in patent: Page/Page column 68

12
[ 53981-24-1 ]
[ 104619-51-4 ]
6-fluorobenzo[d]oxazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In acetonitrile; for 6h;Inert atmosphere; Reflux;	To a of solution 5-fluoro-2-nitrophenol (4.77 mmol, 0.75 g) in methanol (50 mL), PtO2 (0.24 mmol, 0.06 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for fifteen hours. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered quickly over a thin pad of celite which was then immediately washed with methanol (25 mL). The filtrate was concentrated in vacuo yielding an orange residue. The residue was quickly re-dissolved in acetonitrile (50 mL) and <strong>[104619-51-4]di(imidazole-1-yl)methanimine</strong> (11.92 mmol, 1.92 g) was added with constant magnetic stirring. The reaction was then placed under argon atmosphere and gently refluxed for six hours. The reaction was concentrated under reduced pressure and silica gel column chromatography (2:1 hexanes/ethyl acetate) provided a crystalline white solid in a 71% yield. The product of the reduction (2-amino-5-fluorophenol) is air unstable and appropriate measures should be taken to minimize air exposure.
57%	In tetrahydrofuran; at 60℃; for 72h;	Step 1: To a solution of 2-amino-5-fluorophenol (127 mg, 1 mmol) in anhydrous THF (5 mL) was added (di-imidazol-1-yl)-methyleneamine (prepared in example 20, 161 mg, 1 mmol) and the resulting solution was heated at 60 C. for 3 days. The reaction was diluted with ethyl acetate (20 mL) and washed with H2O, saturated aqueous NH4Cl and saturated aqueous NaCl and dried over Na2SO4. The mixture was concentrated in vacuo. Purification by chromatography (silica, 50% ethyl acetate/hexanes) afforded 6-fluorobenzooxazol-2-ylamine (87 mg, 57%): 1H NMR (300 MHz, MeOH) delta ppm 3.29 (s, 2H) 6.01 (ddd, J=9.89, 8.57, 2.45 Hz, 1H) 6.12 (dd, J=8.01, 2.54 Hz, 1H) 6.29 (dd, J=8.57, 4.80 Hz, 1H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3521 - 3525
[2]Patent: US2012/149718,2012,A1 .Location in patent: Page/Page column 43

13
[ 201230-82-2 ]
[ 53981-24-1 ]
[ 2923-94-6 ]

Yield	Reaction Conditions	Operation in experiment
96 %Chromat.	With oxygen In 1,2-dimethoxyethane at 110℃; for 4h;

Reference： [1]Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi [Green Chemistry, 2013, vol. 15, # 3, p. 608 - 611]

14
[ 53981-24-1 ]
[ 103361-99-5 ]

Reference： [1]Patent: WO2014/78802,2014,A1

15
[ 19213-72-0 ]
[ 53981-24-1 ]
[ 2923-94-6 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 59594 - 59602

16
[ 3054-95-3 ]
[ 53981-24-1 ]
[ 135838-04-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With hydrogenchloride; In water; at 111℃; for 24.0h;	General procedure: A 1N HCl solution (82.5 mL) was added to the aniline (~1 mmol) in a round bottom flask. To this was added acrolein diethyl acetal (2.5 mmol). The resulting solution was refluxed at 111 C for 24 hours. After cooling to room temperature, the solution was neutralized (pH 7-8) by addition of solid Na2CO3. The product was then extracted into dichloromethane (3 x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was then purified by column chromatography (elution mixture of hexane with ethyl acetate or 15% ethyl acetate/cyclohexane with methanol) to give the desired quinoline product.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 6436 - 6439

17
[ 53981-24-1 ]
[ 530-62-1 ]
[ 2923-94-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	In N,N-dimethyl-formamide at 0 - 60℃; for 4h;	26.1 Step 1: 6-fluorobenzo[d]oxazol-2(3H)-one (26B) Dissolve 26A (10g, 78.67 mmol) in anhydrous DMF (130 mL) and add N,N'-carbonyldimidazole (15.31 g, 94.40 mmol) dmf (100 mL) solution dropwise under the ice bath, add up, 60 °C reaction for 4 h. Cooled to room temperature, 600mL of water was added, extracted with EA (100mL X 4), backwashed with saturated saline combined with the organic layer, dried anhydrous sodium sulfate, and the residue was separated and purified by silica gel column chromatography after concentration (PE:EA(v/v) = 3:1) to give title compound 26B (11g, 91%).
	In N,N-dimethyl-formamide at 60℃; for 2h;

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - WO2022/42591, 2022, A1 Location in patent: Paragraph 72-73
[2]Bach, Anders; Pizzirani, Daniela; Realini, Natalia; Vozella, Valentina; Russo, Debora; Penna, Ilaria; Melzig, Laurin; Scarpelli, Rita; Piomelli, Daniele [Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9258 - 9272]

18
[ 32315-10-9 ]
[ 53981-24-1 ]
[ 2923-94-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With pyridine In tetrahydrofuran at 5 - 20℃; for 3.5h;

Reference： [1]Zhang, Hao; Liu, Kechang; Liu, Ruiquan; Li, Qibo; Li, Yongqiang; Wang, Qingmin; Liu, Shangzhong [Chinese Journal of Chemistry, 2015, vol. 33, # 7, p. 749 - 755]

19
[ 17624-07-6 ]
[ 91983-14-1 ]
[ 53981-24-1 ]
[ 1240495-78-6 ]

Yield	Reaction Conditions	Operation in experiment
54%		A DMF solution (2 mL) containing 4-fluoro-2-hydroxyniline (127 mg, 1 mmol), 6-mercaptonicotinic acid (155mg, 1 mmol) and EEDQ (248 mg, 1 mmol) was stirred under N2 overnight at room temperature. 2-Bromomethylphenylboronic acid (215 mg, 1mmol) was added to the reaction mixture for another 16 hours at room temperature. The solventwas then removed by rotary evaporation, and the residue dissolved in EtOAc (25 mL), The organic layer was washedwith H2O, 10% Na2CO3, H2O, 1 NHCl, H2O, brine, and dried over Na2SO4, The organic layer was filtered and evaporatedto yield 215 mg (54%) as a dark glass. ESI-MS m/x = 398.94 [M+H]+

Reference： [1]Patent: EP2942346,2015,A1 .Location in patent: Paragraph 0212; 0213

20
[ 53981-24-1 ]
[ 1850312-96-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sulfuric acid; nitric acid In dichloromethane at -10℃; for 2h;	14.1 Step 1) 2-amino-5-fluoro-4-nitrophenol Step 1) 2-amino-5-fluoro-4-nitrophenol A solution of 2-amino-5-fluorophenol (5.5 g, 42.9 mmol) in DCM (15 mL) was cooled to -10 , and a mixed acid of concentrated nitric acid (2.8 g, 45.0 mmol) and concentrated sulfuric acid (10 mL) was added dropwise. After the addition, the mixture was stirred for 2 hours. The reaction mixture was poured into ice (50 g) , and the resulting mixture was adjusted to pH 6-7 with aqueous NaOH (1 M) and diluted with EtOAc (250 mL) . The mixture was separated. The organic layer was washed with water (50 mL × 2) and saturated aqueous NaCl (50 mL) , dried over anhydrous Na2SO4. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE : EtOAc (V : V) 5 : 1) to give 2-amino-5-fluoro-4-nitrophenol as a light yellow solid (6.0 g, 81) .[0875]MS (ESI, pos. ion) m/z: 173.0 [M+H]+.

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2015/197028, 2015, A1 Location in patent: Paragraph 0084

21
[ 53981-24-1 ]
[ 61172-66-5 ]
C₁₆H₁₉FN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of EDCI?HCl (240.0 mg, 1.25 mmol) in DMF (3.1 mL) and CH2Cl2 (3.1 mL) were successively added OxymaPure (177.6 mg, 1.25 mmol) and S6 (266.7 mg, 1.25 mmol) at 0 C. After stirring the reaction mixture for 5 min, 2-amino-5-fluorophenol (159.0 mg, 1.25 mmol) and DIPEA (238 muL, 1.63 mmol) were added, and the resulting mixture was stirred for 10 min at the same temperature. The reaction mixture was warmed to room temperature and stirred for 8 h. The volatiles were removed under reduced pressure. The residue was diluted with ethyl acetate and 1 N HCl aq. was added. The resulting mixture was extracted with ethyl acetate twice, the combined organic layers were washed with aqueous saturated NaHCO3 twice, H2O, brine and dried over Na2SO4. After filtration, the residue was concentrated under reduced pressure and dried in vacuo to give crude amide as brown oil. To the amide in CH3CN (6 mL) and H2O (120 muL) was added BiCl3 (788.0 mg, 2.50 mmol). After the reaction mixture was stirred for 2 h at 55 C, NaHCO3 powder (1.05 g) was added and filtrate was concentrated under reduced pressure to give crude S7 as brown oil. To a solution of EDCI?HCl (216.0 mg, 1.13 mmol) in DMF (3 mL) and CH2Cl2 (3 mL) were successively added OxymaPure (160.0 mg, 1.13 mmol) and 2-fluoro-5-hydroxybonzoic acid (176.0 mg, 1.13 mmol) at room temperature. After stirring the reaction mixture for 5 min, crude S7 in DMF (1 mL) and DIPEA (244 muL, 1.69 mmol) were added, and the resulting mixture was stirred for 12 h at room temperature. The volatiles were removed under reduced pressure. The residue was diluted with ethyl acetate and 1 N HCl aq. was added. The resulting mixture was extracted with ethyl acetate twice, the combined organic layers were washed with aqueous saturated NaHCO3 twice, H2O, brine, then dried over Na2SO4. Filtrate was concentrated and the resulting residue was purified by silica gel chromatography (acetone/n-hexane = 12/88 to 100/0) to give 1e (173.2 mg, 480.7 mumol, 38% over 3 steps) as a white amorphous.White amorphous; [alpha]D27 -5.2 (c 0.38, CH3OH); 1H NMR (400 MHz, CD3OD) delta 7.80 (dd, J = 8.8, 6.1 Hz, 1H), 7.22 (dd, J = 5.9, 3.2 Hz, 1H), 7.06 (dd, J = 10.6, 8.9 Hz, 1H), 6.94 (ddd, J = 8.9, 4.2, 3.2 Hz, 1H), 6.60 (dd, J = 10.0, 2.7 Hz, 1H), 6.55 (ddd, J = 8.8, 8.6, 2.7 Hz, 1H), 4.91 (dd, J = 7.1, 6.0 Hz, 1H), 2.91 (ddd, J = 16.9, 6.0, 2.7 Hz, 1H), 2.84 (ddd, J = 16.9, 7.1, 2.7 Hz, 1H), 2.44 (t, J = 2.7 Hz, 1H); 13C NMR (100 MHz, CD3OD) delta 170.4, 166.4 (d, J = 2.8 Hz), 161.7 (d, J = 240.6 Hz), 155.3 (d, J = 238.4 Hz), 155.1 (d, J = 2.2 Hz), 151.0 (d, J = 10.9 Hz), 124.5 (d, J = 10.2 Hz), 123.2, 123.0 (d, J = 2.2 Hz), 121.0 (d, J = 8.8 Hz), 118.0 (d, J = 25.5 Hz), 117.2 (d, J = 2.2 Hz), 106.5 (d, J = 21.9 Hz), 103.7 (d, J = 24.8 Hz), 79.9, 72.7, 54.4, 22.7; 19F NMR (376 MHz, CD3OD) delta -118.1, -127.6; IR (KBr) nu 3305, 1639, 1601, 1528, 1510, 1455, 1259, 1243 cm-1; HRMS (ESI) calcd. for C18H14N2O4F2Na m/z 383.0814 [M+Na]+, found 383.0801.

Reference： [1]Tetrahedron,2017,vol. 73,p. 1517 - 1521

22
[ 90923-75-4 ]
[ 53981-24-1 ]
6-fluoro-2-(1-methyl-1H-indol-5-yl)benzo[d]oxazole [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2017,vol. 8,p. 1519 - 1529

23
[ 90923-75-4 ]
[ 53981-24-1 ]
C₁₆H₁₃FN₂O [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2017,vol. 8,p. 1519 - 1529

24
[ 53981-24-1 ]
[ 96-34-4 ]
[ 103361-99-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride; potassium carbonate; In N,N-dimethyl-formamide; at 50 - 80℃;	A certain amount of DMF, potassium carbonate, and C6H6FNO and potassium fluoride obtained in step (1) were sequentially added to the reactor.KF, a certain amount of methyl chloroacetate was added dropwise, and the dropping was controlled for 2 to 3 hours without significant exotherm.After the completion of the addition of 50-80 C reaction for 4 hours, the mixture gradually turned yellow, sampling raw materials less than 0.5%;After passing the filter to remove the potassium salt,Filtrate recovery DMF,After recycling, add a certain amount of methanol, warm up to 60-70 degrees, heat for 30 minutes, and start cooling down to 10-20 degrees.Filter to give Intermediate 2;

Reference： [1]Patent: CN107459495,2017,A .Location in patent: Paragraph 0036; 0038; 0048; 0049

25
[ 53981-24-1 ]
[ 36743-66-5 ]
[ 143708-36-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	at 0℃; for 6h;	Synthesis of compounds 1a-1h General procedure: General Method B: To the solution of substituted 2-aminophenol (1.0 equiv.) or substituted benzene-1, 2-diamine(1.0 equiv.) in DCM (or CH3OH), Int 1 (1.5 equiv.) was added and stirred at 0°C overnight. The mixture was filteredwith celite. The filtrate was concentrated, purified by silica gel chromatography (EtOAc:hexane = 1:1) to afford thedesired products.

Reference： [1]Liu, Hao; Chen, Li; Zhou, Fei; Zhang, Yun-Xiao; Xu, Ji; Xu, Meng; Bai, Su-Ping [Bioorganic and Medicinal Chemistry, 2019, vol. 27, # 14, p. 3089 - 3096]

26
[ 53981-24-1 ]
[ 56346-41-9 ]

Reference： [1]Patent: CN110511220,2019,A
[2]Molecules,2020,vol. 25
[3]Patent: WO2021/188769,2021,A1

27
[ 53981-24-1 ]
[ 87-66-1 ]
C₁₂H₆FNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With 3,4,5-trihydroxybenzoic acid; oxygen; sodium carbonate; manganese(ll) chloride In water at 10℃; for 4h;	Synthesis of 2-hydroxyphenoloxazin-3-one: General procedure: In a 150 mL reactor, put 2.18 g o-aminophenol, 1.88 g catechol, 2.2 mg gallic acid, 0.3 g iron sulfate, 0.25 g copper carbonate, 80 mg NaOH and 60 mL water. Heat to 40°C with stirring, add oxygen, keep the pressure in the reactor at 0.3 MPa, stop the reaction after 20 hours of reaction, cool to room temperature, extract with 3 × 15 mL of ethyl acetate, combine ethyl acetate layers, remove by rotary evaporation Ethyl acetate, the remaining solid was recrystallized with isopropanol, suction filtered, and dried to obtain 3.6g of black solid. The structure of the product was determined to be 2-hydroxyphenoloxazin-3-one by NMR (see attached picture), MS, etc. , The yield was 87%, and the purity of the product analyzed by liquid chromatography was 98%.

Reference： [1]Current Patent Assignee: ZHENGZHOU UNIVERSITY - CN111233781, 2020, A Location in patent: Paragraph 0025; 0028

28
[ 53981-24-1 ]
[ 488-17-5 ]
7-fluoro-2-hydroxy-4-methyl-3H-phenoxazin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With 3,4,5-trihydroxybenzoic acid; oxygen; manganese(II) acetate; sodium hydroxide In water at 25℃; for 0.866667h; Sonication; Autoclave; Green chemistry; regioselective reaction;

Reference： [1]Li, Wenhao; Duan, Wenxue; Tang, Qingxuan; Li, Zhan-Ting; Yang, Guanyu [Green Chemistry, 2021, vol. 23, # 3, p. 1136 - 1139]

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[ 53981-24-1 ] Synthesis Path-Upstream 1~12

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