[ CAS No. 198203-94-0 ] {[proInfo.proName]}

Name: 198203-94-0|2-Fluoro-3-methoxybenzonitrile|98%
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SKU: A938629
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Quality Control of [ 198203-94-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 198203-94-0 ]

SDS Specification

Alternatived Products of [ 198203-94-0 ]

Product Details of [ 198203-94-0 ]

CAS No. :	198203-94-0	MDL No. :	MFCD09839223
Formula :	C₈H₆FNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MTZXEJOKWAFGGH-UHFFFAOYSA-N
M.W :	151.14	Pubchem ID :	10701985
Synonyms :

Calculated chemistry of [ 198203-94-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	37.61
TPSA :	33.02 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) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.8
Log Po/w (XLOGP3) :	1.71
Log Po/w (WLOGP) :	2.13
Log Po/w (MLOGP) :	1.55
Log Po/w (SILICOS-IT) :	2.21
Consensus Log Po/w :	1.88

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.19
Solubility :	0.971 mg/ml ; 0.00643 mol/l
Class :	Soluble
Log S (Ali) :	-2.02
Solubility :	1.45 mg/ml ; 0.00957 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.87
Solubility :	0.203 mg/ml ; 0.00134 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.43

Safety of [ 198203-94-0 ]

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

Application In Synthesis of [ 198203-94-0 ]

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

Upstream synthesis route of [ 198203-94-0 ]
Downstream synthetic route of [ 198203-94-0 ]

[ 198203-94-0 ] Synthesis Path-Upstream 1~4

1
[ 198203-94-0 ]
[ 103438-88-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 14, p. 4599 - 4604

2
[ 198204-64-7 ]
[ 198203-94-0 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 4, p. 1163 - 1172

3
[ 74-83-9 ]
[ 1000339-24-1 ]
[ 198203-94-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 14, p. 4599 - 4604

4
[ 137654-20-7 ]
[ 198203-94-0 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 4, p. 1163 - 1172

[ 198203-94-0 ] Synthesis Path-Downstream 1~17

1
[ 2365-48-2 ]
[ 198203-94-0 ]
[ 198204-08-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1.5h;Inert atmosphere;	To a mixture of <strong>[198203-94-0]2-fluoro-3-methoxybenzonitrile</strong> (7.000 g, 45.90 mmol) and potassium carbonate (12.802 g, 91.70 mmol) in DMF (50 mL) is added dropwise methyl 2-mercaptoacetate (4.53 mL, 48.10 mmol). The RM is stirred at RT, under nitrogen, for 1.5h. Water is then added, and the resulting suspension is filtered. The separated solid is then washed with water and dried under high vacuum to give methyl 3-amino-7- methoxybenzo[b]thiophene-2-carboxylate as a beige solid (10.200 g, 94%). LC-MS B: tR = 0.90 min; [M+H]+ = 238.07.

Reference： [1]Patent: WO2018/210987,2018,A1 .Location in patent: Page/Page column 87
[2]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 1163 - 1172

2
[ 198204-64-7 ]
[ 198203-94-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 1163 - 1172

3
[ 137654-20-7 ]
[ 198203-94-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 1163 - 1172

4
[ 198203-94-0 ]
[ 198204-38-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 1163 - 1172

5
[ 73183-34-3 ]
[ 198203-94-0 ]
[ 1383985-45-2 ]

Yield	Reaction Conditions	Operation in experiment
	4,4'-di-tert-butyl-2,2'-bipyridine; In hexane; at 25℃;Inert atmosphere;	Intermediate 792-Fluoro-3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile; A flask containing <strong>[198203-94-0]2-fluoro-3-methoxybenzonitrile</strong> (302 mg, 2.00 mmol), 4,4'-di-tert-butyl-2,2'-dipyridyl (8 mg, 0.03 mmol) and bis(pinacolato)diboron (254 mg, 1.0 mmol) was flushed with argon, and then charged with hexane (6 mL). The mixture was then stirred at 25 C. overnight. The reaction mixture was diluted with EtOAc and washed with brine. The organic phase was concentrated and the crude product was purified on a silica column (0-50% EtOAc/n-heptane) to give the title compound (362 mg with 73% purity according to HPLC): 1H NMR (500 MHz, DMSO-d6) delta ppm 7.63-7.55 (m, 2H), 3.93 (s, 3H), 1.31 (s, 12H); MS (EI) m/z 277 M+.

Reference： [1]Patent: US2012/165347,2012,A1 .Location in patent: Page/Page column 41-42

6
[ 74-83-9 ]
[ 1000339-24-1 ]
[ 198203-94-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4599 - 4604

7
[ 198203-94-0 ]
[ 1204176-23-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4599 - 4604

8
[ 198203-94-0 ]
[ 1204112-52-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4599 - 4604

9
[ 198203-94-0 ]
[ 103438-88-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4599 - 4604

10
[ 110-89-4 ]
[ 198203-94-0 ]
[ 1130556-55-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 4h;	Intermediate 54: (3-methoxy-2-(piperidin-l-yl)phenyl)methanamine Step 1: To a solution of <strong>[198203-94-0]2-fluoro-3-methoxybenzonitrile</strong> (CAS: 198203-94-0) (3 mmol) and piperidine (3.6 mmol) in 10 mL of DMF was added K2CO3 (6 mmol). The reaction was stirred at 80 C for 4 h, then cooled to RT. The reaction mixture was then extracted with water and EtOAc, washed with brine, dried over Na2S04, concentrated in vacuo, then purified by prep-TLC to provide 3-methoxy-2-(piperidin-l-yl)benzonitrile as a yellow solid.

Reference： [1]Patent: WO2015/89137,2015,A1 .Location in patent: Page/Page column 51

11
[ 24424-99-5 ]
[ 198203-94-0 ]
(2-fluoro-3-methoxy-benzyl)-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium tetrahydroborate; nickel(II) chloride hexahydrate; In methanol; at 0 - 20℃; for 72h;Inert atmosphere;	2-Fluoro-3-methoxybenzonitrile (500 mg, 3.31 mmol) was dissolved in methanol (40 mL). This solution was cooled to 0 C. Nickel (II) chloride hexahydrate (79 mg, 0.33 mmol) and di-tertbutyl dicarbonate (1.44g, 6.62mmol) were added followed by sodium borohydride (876 mg, 23.16 mmol) portionwise. The reaction mixture was stirred, allowed to warm to rt and stirred for 3 days. The MeOH was removed in vacuo. The residue was dissolved in CHCl3 (150 mL), washed with sat NaHCO3 (aq) (50 mL), water (50mL), brine (50mL), dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography (silica), eluent 20% EtOAc / 80% Pet. Ether, to give a white solid identified as (2-fluoro-3-methoxy-benzyl)- carbamic acid tert-butyl ester (540 mg, 0.2 mmol, 64% yield). [MH]+ = 255.8
64%	With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate; at 0 - 20℃; for 72h;	2- fluoro-3-methoxybenzonitrile (500 mg, 3.31 mmol) was dissolved in methanol (40 mL). This solution was cooled to 0 C. Nickel (II) chloride hexahydrate (79 mg, 0.33 mmol) and di-tertbutyl dicarbonate (1.44g, 6.62mmol) were added followed by sodium borohydride (876 mg, 23.16 mmol) portionwise. The reaction mixture was stirred, allowed to warm to rt and stirred for 3 days. The MeOH was removed in vacuo. The residue was dissolved in CHCI3 (150 mL), washed with sat NaHC03 (aq) (50 mL), water (50mL), brine (50mL), dried (Na2S04) and evaporated in vacuo. The residue was purified by chromatography (silica), eluent 20% EtOAc / 80% Pet. Ether, to give a white solid identified as (2-fluoro-3-methoxybenzyl)-carbamic acid tert-butyl ester (540 mg, 0.2 mmol, 64% yield). [MH]+ = 255.8

Reference： [1]Patent: WO2016/83820,2016,A1 .Location in patent: Page/Page column 45
[2]Patent: WO2017/207983,2017,A1 .Location in patent: Page/Page column 48

12
benzyl (6-hydroxyspiro[3.3]heptane-2-yl)carbamate [ No CAS ]
[ 198203-94-0 ]
benzyl (6-(2-cyano-6-methoxyphenoxy)spiro[3.3]heptan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		Intermediate 1 (93 mg, 0.36 mmol) was dissolved in anhydrous THE (2 mE). The reaction mixture was cooled in ice bath, and potassium tert-butoxide (IM in THF, 0.36 mL, 0.36 nunol) was added. An insoluble guru was formed After 30 miii, 2-fiuoro-3- methoxybenzonitrile (134 mg, 0.89 mmol) was added in one portion. The ice bath was removed and the reaction was stirred at rt for 2 h, then put in the freezer on. The reaction was quenched with water (0. 5mL), concentrated and purified by flash chromatography (0- 100% EtOAc/hexanes gradient) to give Example 208A (110 rng, 79%) as a clear oil.MS(ESI) m/z: 393.1 (M+HY. ?H NMR (400MHz, CDCI3) 7.43 -7.28 (in, 5H). 7.16 -7.02 (m. 3K), 5.07 (s, 2K), 4.82 (d, J=5.l Hz, 11-1), 4.72 (quin, J=7.2 Hz, IH), 423 - 4.00 (m, 1K), 3.85 (s, 3H), 2.54 -2.21 (m, 6H), 1.95 (t, J=i0.i Hz, 1H), 1.86 (t, J=9.7 Hz, IH).

Reference： [1]Patent: WO2017/123860,2017,A1 .Location in patent: Page/Page column 393; 394

13
[ 198203-94-0 ]
tert-butyl (2-(2-cyano-7-methoxybenzo[b]thiophen-3-yl)ethyl)carbamate [ No CAS ]