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[ CAS No. 198967-24-7 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}

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3d Animation Molecule Structure of 198967-24-7

Chemical Structure| 198967-24-7

Chemical Structure| 198967-24-7

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Quality Control of [ 198967-24-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 198967-24-7 ]

Product Details of [ 198967-24-7 ]

CAS No. :	198967-24-7	MDL No. :	MFCD02684304
Formula :	C₉H₁₀FNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WWEPCBKULBKDCS-UHFFFAOYSA-N
M.W :	183.18 g/mol	Pubchem ID :	18357556
Synonyms :

Calculated chemistry of [ 198967-24-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.38
TPSA :	29.54 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.05
Log Po/w (XLOGP3) :	1.53
Log Po/w (WLOGP) :	1.88
Log Po/w (MLOGP) :	2.2
Log Po/w (SILICOS-IT) :	1.23
Consensus Log Po/w :	1.78

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.08
Solubility :	1.51 mg/ml ; 0.00826 mol/l
Class :	Soluble
Log S (Ali) :	-1.76
Solubility :	3.19 mg/ml ; 0.0174 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.48
Solubility :	0.611 mg/ml ; 0.00333 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.73

Safety of [ 198967-24-7 ]

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

Application In Synthesis of [ 198967-24-7 ]

* 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 [ 198967-24-7 ]
Downstream synthetic route of [ 198967-24-7 ]

[ 198967-24-7 ] Synthesis Path-Upstream 1~3

1
[ 6638-79-5 ]
[ 393-52-2 ]
[ 198967-24-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: With triethylamine In dichloromethane at 0℃; for 0.166667 h; Stage #2: at 0 - 20℃;	Triethylamine (5.32 mL, 37.84 mmol) was added dropwise to a solution of Ν,Ο-dimethylhydroxylamine hydrochloride (2.768 g, 28.38 mmol) in anhydrous dichloromethane (45 mL) at 0 °C. After stirring for 10 min, 2-fluorobenzoyl chloride (0.303 mL, 2.52 mmol) in anhydrous dichloromethane (15 mL) was added dropwise. The reaction mixture was returned to room temperature and stirred for 5 h. The reaction mixture was quenched with water (60 mL) and the products were extracted with dichloromethane (2 x 60 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient 93:7 to 60:40) afforded 2-Fluoro-N-methoxy-N-methyl-benzamide (3.1 16, 17 mmol) in a 90percent yield. [0
90%	Stage #1: With triethylamine In dichloromethane at 0℃; for 0.166667 h; Inert atmosphere Stage #2: at 0 - 20℃; for 5 h; Inert atmosphere	Triethylamine (5.32 mL, 37.8 mmol) was added dropwise to a solution of N,O-dimethylhydroxylamine hydrochloride (2.77 g, 28.4 mmol) in anhydrous dichloromethane (45 mL) at 0 °C. After stirring for 10 min, 2-flurobenzoyl chloride (0.303 mL, 2.52 mmol) in anhydrous dichloromethane (15 mL) was added dropwise. The reaction mixture was returned to room temperature and stirred for 5 h. The reaction mixture was quenched with water (60 mL) and the products were extracted with dichloromethane (2 * 60 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes/ethyl acetate, gradient 93:7 to 60:40) afforded 2-Fluoro-N-methoxy-N-methyl-benzamide (3.12 g, 17.0 mmol, 90percent yield). ¹H NMR (500 MHz, CDCl₃): δ 7.44-7.38 (2H, m), 7.19 (1H, t, J = 7.5 Hz), 7.10 (1H, t, J = 8.9 Hz), 3.55 (3H, br s), 3.35 (3H, br s). ¹³C NMR (125 MHz, CDCl₃): δ 166.40, 158.66, (d, J = 249 Hz), 131.50, 128.90, 124.11, 123.52 (d, J = 17 Hz), 115.69 (d, J = 21 Hz), 61.21, 32.31. ¹⁹F NMR (470 MHz, CDCl₃): δ -114.04 (1F, s). HRMS (ESI) calculated for C₉H₁₀FNO₂H⁺ (M+H)⁺ 184.07683, found 184.07702.
62%	With pyridine In tetrahydrofuran at 0 - 20℃; for 2.25 h;	N,O-Dimethylhydroxylamine hydrochloride (23.4 g, 240 mmol) was suspended inTHF (100 ml) and cooled to 0 °C under nitrogen. Pyridine (32 ml, 400 mmol) was addedslowly. A solution of 2-fluorobenzoyl chloride (9.5 ml, 80 mmol) in THF (50 ml) was addedover 15 min. The reaction was removed from the ice bath and stirred at rt for 2 h. Water (100ml) and AcOEt (100 ml) were added, and the phases were separated. The aq. phase wasextracted with AcOEt (100 ml). The organic phases were pooled and washed with 1 N HCI (2x 100 ml) and 1 N NaOH (100 ml). After drying over MgSO₄, the sample was concentrated toyield a yellow oil (10.7 g). The oil was purified by vacuum distillation, and a colorless oil wascollected (0.22 torr, 57-59 °C, 9.1 g, 62percent yield)2-fluoro-N-methoxy-N-methylbenzamide¹H-NMR (300MHz, CDCI₃) 53.34 (s, 3H), 3.54 (br, 3H), 7.10 (m, 1H), 7.19 (m, 1H),7.42 (m, 2H)

Reference： [1] RSC Advances, 2013, vol. 3, # 26, p. 10158 - 10162
[2] Patent: WO2013/142038, 2013, A2, . Location in patent: Paragraph 0130
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6974 - 6992
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1415 - 1419
[5] Patent: WO2006/3096, 2006, A1, . Location in patent: Page/Page column 73
[6] Chemical Communications, 2012, vol. 48, # 71, p. 8976 - 8978

2
[ 393-52-2 ]
[ 1117-97-1 ]
[ 198967-24-7 ]

Yield	Reaction Conditions	Operation in experiment
84.6%	With triethylamine In dichloromethane at 0 - 20℃;	To a solution of 2-fluorobenzoyl chloride (50 g, 0.31 mol) in CH₂Cl₂(200 mL) was added N,O-dimethylhydroxylamine (46 g, 0.47 mol), and a solution of triethylamine (127 g, 1.26 mol) in CH₂Cl₂(100 mL) at 0° C. The reaction mixture was warmed slowly to rt, and stirred for 3 h. The mixture was quenched with iced water and extracted with CH₂Cl₂(200 mL). The organic layer was dried over Na₂SO₄, filtered, and concentrated to afford 2-fluoro-N-methoxy-N-methylbenzamide (48 g, yield: 84.6percent).

Reference： [1] Patent: US2010/331320, 2010, A1, . Location in patent: Page/Page column 51; 52

3
[ 6638-79-5 ]
[ 445-29-4 ]
[ 198967-24-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 2 h;	2-Fluoro-N-methoxy-N-methylbenzamide was prepared in 73percent yield according to the Example 1 , Step A substituting 6-bromopicolinic acid for 2-fluorobenzoic acid.

Reference： [1] Patent: WO2015/140133, 2015, A1, . Location in patent: Page/Page column 96

[ 198967-24-7 ] Synthesis Path-Downstream 1~24

1
[ 6638-79-5 ]
[ 393-52-2 ]
[ 198967-24-7 ]

Yield	Reaction Conditions	Operation in experiment
90%		Triethylamine (5.32 mL, 37.84 mmol) was added dropwise to a solution of Nu,Omicron-dimethylhydroxylamine hydrochloride (2.768 g, 28.38 mmol) in anhydrous dichloromethane (45 mL) at 0 C. After stirring for 10 min, 2-fluorobenzoyl chloride (0.303 mL, 2.52 mmol) in anhydrous dichloromethane (15 mL) was added dropwise. The reaction mixture was returned to room temperature and stirred for 5 h. The reaction mixture was quenched with water (60 mL) and the products were extracted with dichloromethane (2 x 60 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient 93:7 to 60:40) afforded 2-Fluoro-N-methoxy-N-methyl-benzamide (3.1 16, 17 mmol) in a 90% yield. [0
90%		Triethylamine (5.32 mL, 37.8 mmol) was added dropwise to a solution of N,O-dimethylhydroxylamine hydrochloride (2.77 g, 28.4 mmol) in anhydrous dichloromethane (45 mL) at 0 C. After stirring for 10 min, 2-flurobenzoyl chloride (0.303 mL, 2.52 mmol) in anhydrous dichloromethane (15 mL) was added dropwise. The reaction mixture was returned to room temperature and stirred for 5 h. The reaction mixture was quenched with water (60 mL) and the products were extracted with dichloromethane (2 * 60 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes/ethyl acetate, gradient 93:7 to 60:40) afforded 2-Fluoro-N-methoxy-N-methyl-benzamide (3.12 g, 17.0 mmol, 90% yield). 1H NMR (500 MHz, CDCl3): delta 7.44-7.38 (2H, m), 7.19 (1H, t, J = 7.5 Hz), 7.10 (1H, t, J = 8.9 Hz), 3.55 (3H, br s), 3.35 (3H, br s). 13C NMR (125 MHz, CDCl3): delta 166.40, 158.66, (d, J = 249 Hz), 131.50, 128.90, 124.11, 123.52 (d, J = 17 Hz), 115.69 (d, J = 21 Hz), 61.21, 32.31. 19F NMR (470 MHz, CDCl3): delta -114.04 (1F, s). HRMS (ESI) calculated for C9H10FNO2H+ (M+H)+ 184.07683, found 184.07702.
62%	With pyridine; In tetrahydrofuran; at 0 - 20℃; for 2.25h;	N,O-Dimethylhydroxylamine hydrochloride (23.4 g, 240 mmol) was suspended inTHF (100 ml) and cooled to 0 C under nitrogen. Pyridine (32 ml, 400 mmol) was addedslowly. A solution of 2-fluorobenzoyl chloride (9.5 ml, 80 mmol) in THF (50 ml) was addedover 15 min. The reaction was removed from the ice bath and stirred at rt for 2 h. Water (100ml) and AcOEt (100 ml) were added, and the phases were separated. The aq. phase wasextracted with AcOEt (100 ml). The organic phases were pooled and washed with 1 N HCI (2x 100 ml) and 1 N NaOH (100 ml). After drying over MgSO4, the sample was concentrated toyield a yellow oil (10.7 g). The oil was purified by vacuum distillation, and a colorless oil wascollected (0.22 torr, 57-59 C, 9.1 g, 62% yield)2-fluoro-N-methoxy-N-methylbenzamide1H-NMR (300MHz, CDCI3) 53.34 (s, 3H), 3.54 (br, 3H), 7.10 (m, 1H), 7.19 (m, 1H),7.42 (m, 2H)

Reference： [1]RSC Advances,2013,vol. 3,p. 10158 - 10162
[2]Patent: WO2013/142038,2013,A2 .Location in patent: Paragraph 0130
[3]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6974 - 6992
[4]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1415 - 1419
[5]Patent: WO2006/3096,2006,A1 .Location in patent: Page/Page column 73
[6]Chemical Communications,2012,vol. 48,p. 8976 - 8978
[7]Organic Letters,2019,vol. 21,p. 7430 - 7434

2
[ 198967-24-7 ]
C₂₄H₂₄ClFN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 48: 4-tert-Butyl-N-[5-chloro-2-(2-fluoro-benzoyi)-pyridin-3-yl]- benzenesulfonamide; [00439] N-(2-Bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-N-methoxymethyl- benzenesulfonamide (140 mg, 300 mmol) was placed in a dry 2-neck 10 mL round-bottom flask. The flask was evacuated and purged with nitrogen, followed by the addition of THF (1 mL). The homogeneous mixture was lowered to -5 C and /PrMgCI (0.33 mL, 2.0 M) was added dropwise. Upon completion of the addition, the reaction was stirred 90 minutes, followed by the slow addition of 2- fluoro-N-methoxy-N-methyl-benzamide (140 mg, 750 mmol). The reaction was stirred overnight, during which the ice-bath warmed to room temperature. The following day, the reaction was quenched with a small quantity of MeOH and the solvents evaporated in vacuo. The residue was subsequently treated with 4.0 M HCI (in dioxane) (1 mL, 4.0 mmol) and H2O (0.33 mL), and then stirred at 80 C for two hours. The resultant solution was diluted with EtOAc, washed with water, saturated sodium bicarbonate, and brine; dried with MgSO4, and evaporated employing reduced pressure. The crude sulfonamide was finally purified via preparatory TLC (20% EtOAc/hexanes) and recrystallization from MeCN/H2O to afford 98 mg of the title compound: 1H NMR (400 MHz, CDCI3) delta 10.6 (s, 1 H), 8.3 (d, 1H), 8.2 (d, 1H), 7.74 (d, 2H), 7.6 (d, 1 H), 7.5 (d, 1 H), 7.43 (d, 2H), 7.42-7.37 (m, 2H), 1.26 (s, 9H); MS (ES) M+H expect 447.1 , found 447.5.

Reference： [1]Patent: WO2006/76644,2006,A2 .Location in patent: Page/Page column 121

3
[ 198967-24-7 ]
3-bromo-2-(diethoxymethyl)-benzo[b]furan [ No CAS ]
2-(diethoxymethyl)-3-(2-fluorobenzoyl)-benzo[b]furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butyl lithium; In n-heptane; water; toluene;	EXAMPLE 13 2-(Diethoxymethyl)-3-(2-fluorobenzoyl)-benzo[b]furan To a solution of 3 g of 3-bromo-2-(diethoxymethyl)-benzo[b]furan in 80 ml of dry ether under nitrogen at -100 C was added 17.4 ml of a 1.7 M solution of tert-butyllithium in hexanes. The solution was stirred at the low temperature for 2 h then a solution of 2.76 g of <strong>[198967-24-7]N-methoxy-N-methyl-2-fluorobenzamide</strong> in 20 ml of dry ether was added and the solution stirred at the low tempertature for 10 min. The solution was then allowed to slowly warm to 0 C., water was added and the organic layer was separated, washed with water and dried over sodium sulfate and evaporated. Gravity chromatography eluding 0 to 50% toluene in heptane afforded 0.91 g of 2-(diethoxymethyl)-3-(2-fluorobenzoyl)-benzo[b]furan as an oil, 1 H-NMR (200 MHz, CDCl3) d 5.76 (CHOEt). In a similar manner were prepared: 2-(Diethoxymethyl)-5-(2-fluorobenzoyl)-thiophene, starting from 2-bromo-5-(diethoxymethyl)-thiophene (see D. J. Chadwick, J. Chambers, P. K. Hodgson, G. D, Meakins and R. L. Snowden, J. Chem. Soc., Perkin Trans. 1, 1994, 2735), 1 H-NMR (200 MHz, CDCl3) d 5.75 (CHOEt),

Reference： [1]Patent: US6080773,2000,A

4
[ 198967-24-7 ]
[ 108-36-1 ]
[ 698982-90-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1415 - 1419

5
[ 198967-24-7 ]
[ 106-37-6 ]
[ 59396-43-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1415 - 1419

6
[ 393-52-2 ]
[ 1117-97-1 ]
[ 198967-24-7 ]

Yield	Reaction Conditions	Operation in experiment
84.6%	With triethylamine; In dichloromethane; at 0 - 20℃;	To a solution of 2-fluorobenzoyl chloride (50 g, 0.31 mol) in CH2Cl2 (200 mL) was added N,O-dimethylhydroxylamine (46 g, 0.47 mol), and a solution of triethylamine (127 g, 1.26 mol) in CH2Cl2 (100 mL) at 0 C. The reaction mixture was warmed slowly to rt, and stirred for 3 h. The mixture was quenched with iced water and extracted with CH2Cl2 (200 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford 2-fluoro-N-methoxy-N-methylbenzamide (48 g, yield: 84.6%).

Reference： [1]Patent: US2010/331320,2010,A1 .Location in patent: Page/Page column 51; 52

7
[ 198967-24-7 ]
[ 1826-67-1 ]
[ 89638-21-1 ]

Yield	Reaction Conditions	Operation in experiment
58.4%	In tetrahydrofuran; at -78 - 20℃;	A solution of <strong>[198967-24-7]2-fluoro-N-methoxy-N-methylbenzamide</strong> (16 g, 87.4 mmol) in THF (150 mL) was cooled to -78 C. Vinylmagnesium bromide (120 mL, 120 mmol) was slowly added, and the mixture stirred at -78 C. for 10 min, slowly warmed to rt, and stirred for another 3 h. The reaction mixture was quenched with 1 N aq HCl (100 mL) at 0 C. The aqueous layer was extracted with EtOAc (100 mL). The combined organic phase was washed with brine (50 mL), dried over Na2SO4, and concentrated. The residue was purified by column chromatography to afford 1-(2-fluorophenyl)-prop-2-en-1-one (7.6 g, yield: 58.4%) as a colorless oil.

Reference： [1]Patent: US2010/331320,2010,A1 .Location in patent: Page/Page column 51; 52

8
[ 198967-24-7 ]
C₈H₁₂O₃^(2-)*Li⁽¹⁺⁾*Na⁽¹⁺⁾ [ No CAS ]
[ 1394949-24-6 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 8976 - 8978

9
[ 198967-24-7 ]
[ 141-32-2 ]
(E)-butyl 3-(2-(methoxy(methyl)carbarmoyl)-3-fluorophenyl)acrylate [ No CAS ]
(Z)-butyl 3-(2-(methoxy(methyl)carbarmoyl)-3-fluorophenyl)acrylate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1724 - 1728

10
[ 198967-24-7 ]
[ 1458033-38-9 ]

Reference： [1]Patent: WO2013/142038,2013,A2

11
[ 198967-24-7 ]
[ 626-39-1 ]
[ 1458033-50-5 ]

Yield	Reaction Conditions	Operation in experiment
50%		Tert-butyllithium in pentane (1.6M, 7.72 mL) was added dropwise to a solution of 1 ,3,5 tribromobenzene (0.972 g, 3.09 mmol) in anhydrous ether (30 mL) at -78 C under a flow of nitrogen gas. After 2 h, 2-Fluoro-/V-methoxy-/V- methyl-benzamide (1.132 g, 6.18 mmol) dissolved in anhydrous ether (5 mL) was added dropwise and the reaction mixture was allowed to slowly come to room temperature and stirred for 24 h. After 24 h, the reaction mixture was quenched with water (30 ml_) and the products were extracted with ether (2 x 50 ml_). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient 95:5 to 60:40) afforded 2-1 ,3-bis(2-fluoro-benzoyl)-5-bromobenzene 10 (0.617 g, 6.18 mmol) in a 50% yield.

Reference： [1]Patent: WO2013/142038,2013,A2 .Location in patent: Paragraph 0131

12
[ 198967-24-7 ]
1,3-bis(3-fluorobenzoyl)-5-bromobenzene thiosemicarbazone [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6974 - 6992

13
[ 198967-24-7 ]
[ 626-39-1 ]
1,3-bis(3-fluorobenzoyl)-5-bromobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		tert-Butyllithium in pentane (1.6 M, 7.72 mL) was added dropwise to a solution of 1,3,5-tribromobenzene (0.972 g, 3.09 mmol) in anhydrous ether (30 mL) at -78 C under a flow of nitrogen gas. After 2 h, <strong>[198967-24-7]2-fluoro-N-methoxy-N-methyl-benzamide</strong> (1.132 g, 6.18 mmol) dissolved in anhydrous ether (5 mL) was added dropwise and the reaction mixture was allowed to slowly come to room temperature and stirred for 24 h. After 24 h, the reaction mixture was quenched with water (30 mL) and the products were extracted with ether (2 * 50 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes/ethyl acetate, gradient 95:5 to 60:40) afforded 1,3-bis(3-fluorobenzoyl)-5-bromobenzene (0.617 g, 6.18 mmol, 50% yield). 1H NMR (500 MHz, CDCl3): delta 8.16 (2H, m), 8.12 (1H, pentet, J = 1.4 Hz), 7.61-7.56 (4H, m), 7.30 (2H, td, J = 7.5 Hz, 1.0 Hz), 7.20-7.16 (2H, m). 13C NMR (125 MHz, CDCl3): delta 191.23, 160.40 (d, J = 254 Hz), 139.67, 133.61, 134.29 (d, J = 8.6 Hz), 131.12 (d, J = 1.9 Hz), 129.31, 125.79 (d, J = 13.8 Hz), 124.79 (d, J = 3.8 Hz), 123.18, 116.70 (d, J = 21 Hz). 19F NMR (470 MHz, CDCl3): delta -109.73 to -109.78 (1F, m). HRMS (ESI) calculated for C20H11BrF2O2H+ (M+H)+ 400.99833, found 400.99857.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6974 - 6992

14
[ 6638-79-5 ]
[ 445-29-4 ]
[ 198967-24-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; for 2h;	2-Fluoro-N-methoxy-N-methylbenzamide was prepared in 73% yield according to the Example 1 , Step A substituting 6-bromopicolinic acid for 2-fluorobenzoic acid.

Reference： [1]Patent: WO2015/140133,2015,A1 .Location in patent: Page/Page column 96

15
[ 198967-24-7 ]
[ 107-30-2 ]
[ 925211-28-5 ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 7584 - 7587

16
[ 198967-24-7 ]
[ 593-71-5 ]
[ 18156-74-6 ]
2-chloro-1-(2-fluorophenyl)-N-methoxy-N-methyl-1-[(trimethylsilyl)oxy]ethanamine [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 9498 - 9501

17
[ 198967-24-7 ]
[ 218601-55-9 ]
C₂₃H₂₈FNO₃ [ No CAS ]
C₂₃H₂₈FNO₃ [ No CAS ]

Reference： [1]ChemSusChem,2019,vol. 12,p. 1147 - 1154

18
[ 198967-24-7 ]
[ 65864-64-4 ]
[ 1378683-82-9 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8261 - 8265

19
[ 198967-24-7 ]
(Z)-1-(2-fluorophenyl)pent-4-en-1-one O-methyl oxime [ No CAS ]
(E)-1-(2-fluorophenyl)pent-4-en-1-one O-methyl oxime [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 7430 - 7434

20
[ 5162-44-7 ]
[ 198967-24-7 ]
[ 1338961-41-3 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 7430 - 7434

21
[ 198967-24-7 ]
[ 591-51-5 ]
2-chloro-2-(2-fluorophenyl)-2-phenylacetaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0.5 h / -78 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / -20 °C / Flow reactor 2.2: -20 °C / Flow reactor 2.3: Amberlyst 15 / 20 °C

Reference： [1]Colella, Marco; Degennaro, Leonardo; Luisi, Renzo; Musci, Pantaleo; Romanazzi, Giuseppe; Sivo, Alessandra [Organic Letters, 2020, vol. 22, # 9, p. 3623 - 3627]

22
[ 198967-24-7 ]
[ 591-51-5 ]
[ 342-24-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at -78℃; for 0.5h;

Reference： [1]Colella, Marco; Degennaro, Leonardo; Luisi, Renzo; Musci, Pantaleo; Romanazzi, Giuseppe; Sivo, Alessandra [Organic Letters, 2020, vol. 22, # 9, p. 3623 - 3627]

23
[ 198967-24-7 ]
7-bromo-2-methyl-1,5-napthyridine [ No CAS ]
2-(7-bromo-1,5-naphthyridin-2-yl)-1-(2-fluorophenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere;	137.1 Example 137 Step 1: In an oven-dried flask was charged 2-fluoro-N-methoxy-N-methylbenzamide (82 mg, 0.448 mmol) and 1 (100 mg, 0.448 mmol) . The resulting mixture was purged with nitrogen and THF (1.1 mL) was added. The mixture was cooled to -78° C. and potassium bis(trimethylsilyl)amide, 0.5M in toluene (1.076 mL, 0.538 mmol) was added dropwise over a course of 10 min resulting in a deep red mixture. The resultant mixture was stirred at -78° C. for 2 h. Dry ice bath was removed and the mixture was warmed to room temperature and stirred at room temperature for 2 h before being quenched with water (5 mL). The mixture was extracted with EA (3*7 mL), dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (EA in hexanes 0 to 100% gradient) to yield intermediate 2-(7-bromo-1,5-naphthyridin-2-yl)-1-(2-fluorophenyl)ethan-1-one 152 (23 mg, 15%) as a yellow solid. [M+H]+ calcd for C16H10BrFN2O 344.00, found 345.0.

Reference： [1]Current Patent Assignee: THERAVANCE BIOPHARMA, INC. - US2020/188370, 2020, A1 Location in patent: Paragraph 0479; 0801; 0802

24
[ 198967-24-7 ]
[ 75-09-2 ]
2,2‐dichloro‐1‐(2‐fluorophenyl)ethan‐1‐one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With methyllithium lithium bromide; diisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; chemoselective reaction;

Reference： [1]Malik, Monika; Pace, Vittorio; Senatore, Raffaele; Touqeer, Saad; Urban, Ernst [Advanced Synthesis and Catalysis, 2020, vol. 362, # 22, p. 5056 - 5061]

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