23077-43-2|5-Fluoro-1H-indole-3-carboxylic acid| Ambeed

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Quality Control of [ 23077-43-2 ] Purity: 98% SDS Specification

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Product Details of [ 23077-43-2 ]

CAS No. :	23077-43-2
Formula :	C₉H₆FNO₂
M.W :	179.15
SMILES Code :	O=C(C1=CNC2=C1C=C(F)C=C2)O
MDL No. :	MFCD00047171
InChI Key :	SDZBAXLIHRBNOV-UHFFFAOYSA-N
Pubchem ID :	17750930

Safety of [ 23077-43-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 23077-43-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	45.22
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	53.09 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.11
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.09
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.43
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.5
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.29
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.88

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.71
Solubility	0.346 mg/ml ; 0.00193 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.83
Solubility	0.262 mg/ml ; 0.00146 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.94
Solubility	0.208 mg/ml ; 0.00116 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.91 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.41

Application In Synthesis of [ 23077-43-2 ]

* 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.

Downstream synthetic route of [ 23077-43-2 ]

[ 23077-43-2 ] Synthesis Path-Downstream 1~35

2
[ 23077-43-2 ]
[ 530-62-1 ]
(5-fluoro-1<i>H</i>-indol-3-yl)-imidazol-1-yl-methanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1125 - 1139.

3
[ 399-52-0 ]
[ 407-25-0 ]
[ 23077-43-2 ]

Yield	Reaction Conditions	Operation in experiment
75%		Reference Example 27; 5-Fluoro-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yI)-lJ?-indole; A solution of 5-fluoroindole (5 g, 37.0 mmol) in DMF (40 mL) was treated at 0 0C with trifluoroacetic anhydride (6.1 mL, 42.6 mmol). After 30 min, the reaction was poured into water and the resulting precipitate collected by filtration, washed with water, then dried in vacuo. The solid was then dissolved in 10% aqueous NaOH (200 mL) and heated at reflux for 1 h. The reaction mixtur was then cooled, washed with dichloromethane and acidified with aqueous HCl. The resulting white precipitate was collected by filtration, washed with water, taken up in dichloromethane, washed with water, dried (MgSO4) and evaporated in vacuo. The resulting material (5 g, 75%) was dissolved in methanol (80 mL) and treated with concentrated sulphuric acid (2 mL) <n="75"/>then heated at reflux overnight. The reaction was cooled and the resulting precipitate collected, washed with water and evaporated in vacuo to give 5-fluoro-lH-indole-3- carboxylic acid methyl ester as a peach-coloured solid (4.5 g, 83 %).
68%	In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	[00194] This compound was prepared according to the procedure described in the Journal of Medicinal Chemistry 2014, 57(17), 7293 - 7316. Trifluoroacetic anhydride (38 mL, 56.0 g, 0.27 mol) was added dropwise to a solution of 5-fluoro-lH-indole (30.0 g, 0.22 mol) in DMF (300 mL) over 0.5 h at 0C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was quenched with water (1 L), after which solids began to form, the mixture was stirred for 0.5 h, then filtered. The solid was collected, washed with water (200 mL><3), then added to aqueous sodium hydroxide (20%, 150 mL, 0.75 mol) and heated under reflux for 8 h. The reaction mixture was cooled and acidified with aqueous 3N HC1 to pH of 3 whereupon a precipitate was produced. The solid was collected by filtration, washed with water (200 mLx3), dried to afford compound 2 (27.1 g, 68% yield) as off-white solid

References: [1]Patent: WO2007/122410,2007,A1 .Location in patent: Page/Page column 73-74.
[2]Patent: WO2019/99977,2019,A2 .Location in patent: Paragraph 00191; 00194.

4
[ 67-56-1 ]
[ 23077-43-2 ]
[ 310886-79-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	sulfuric acid;Heating / reflux;	Reference Example 27; 5-Fluoro-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yI)-lJ?-indole; A solution of 5-fluoroindole (5 g, 37.0 mmol) in DMF (40 mL) was treated at 0 0C with trifluoroacetic anhydride (6.1 mL, 42.6 mmol). After 30 min, the reaction was poured into water and the resulting precipitate collected by filtration, washed with water, then dried in vacuo. The solid was then dissolved in 10% aqueous NaOH (200 mL) and heated at reflux for 1 h. The reaction mixtur was then cooled, washed with dichloromethane and acidified with aqueous HCl. The resulting white precipitate was collected by filtration, washed with water, taken up in dichloromethane, washed with water, dried (MgSO4) and evaporated in vacuo. The resulting material (5 g, 75%) was dissolved in methanol (80 mL) and treated with concentrated sulphuric acid (2 mL) <n="75"/>then heated at reflux overnight. The reaction was cooled and the resulting precipitate collected, washed with water and evaporated in vacuo to give 5-fluoro-lH-indole-3- carboxylic acid methyl ester as a peach-coloured solid (4.5 g, 83 %).

References: [1]Patent: WO2007/122410,2007,A1 .Location in patent: Page/Page column 73-74.

5
[ 23077-43-2 ]
5-Fluoro-1H-indole-3-carboxylic acid (1R,7aS)-1-(hexahydro-pyrrolizin-1-yl)methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1125 - 1139.

6
[ 399-52-0 ]
[ 124-38-9 ]
[ 23077-43-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With lithium tert-butoxide; In N,N-dimethyl-formamide; at 100℃; under 760.051 Torr; for 24h;	General procedure: In a dried two-necked test tube was charged with LiOtBu (160 mg, 2.00 mmol) and indole 1a (23.4 mg, 0.4 mmol). The reaction vessel was evacuated under high vacuum and the atmosphere was replace with a balloon of CO2. Then DMF (2 mL) was added and the mixture was stirred for 24 h at 100C. Then the result mixture was cooled and carefully quenched with a solution of HCl (2 N) and extracted with EtOAc (5x). The combined organic layers were washed with water (2x), brine (1x) and dry over MgSO4. The dried organics were concentrated under reduce pressure and the residue was purified by preparative TLC (hexane:acetone = 1:1) to afford the desired product 2a (153.0 mg, 95%) as a white solid.

References: [1]Organic Letters,2012,vol. 14,p. 5326 - 5329,4.
[2]Heterocycles,2015,vol. 90,p. 1196 - 1204.

7
[ 399-52-0 ]
[ 23077-43-2 ]

References: [1]Patent: EP2548864,2013,A1 .
[2]Patent: WO2013/14102,2013,A1 .
[3]CrystEngComm,2013,vol. 15,p. 7490 - 7497.
[4]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316.
[5]Patent: JP2017/171619,2017,A .

8
[ 1019117-66-8 ]
[ 23077-43-2 ]
[ 1419517-29-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	To a stirred solution of indolic amine (gb) (72 mg, 0.3 mmol) and <strong>[23077-43-2]5-fluoro-1H-indole-3-carboxylic acid</strong> (2f) (59 mg, 0.33 mmol) in 5 mL of dry CH2Cl2, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 5 mg, 0.33 mmol) was added at room temperature. The resulting mixture was stirred overnight. Then CH2Cl2 was evaporated then EtOAc (20 mL) and a 1M aqueous solution of hydrochloric acid (20 mL) were added. After extraction, organic phase was washed with an aqueous solution of hydrochloric acid, a 5% aqueous solution of Na2CO3, brine, dried over anhydrous MgSO4, filtered, and concentrated under vacuum. Purification of the crude product by column chromatography using EtOAc-pentane (from 1/9 to 8/2) yielded the pure bis-indole 5 (60 mg, 0.226 mmol) as a beige foam. Yield: 50%. IR (neat): 3455, 3240, 2975, 2870, 1740, 1595, 1530, 1460, 1425, 1205, 1170, 1080, 1005, 930, 850, 760 cm-1. 1H NMR (300 MHz, CD3OD-DMSO-d6): delta = 1.60 (d, J= 6.8 Hz, 3H), 5.49 (q, J= 6.8 Hz, 1H), 6.99 (dt, J = 2.6 and 9.0 Hz, 1H), 7.09 (dd, J = 1.9 and 8.7 Hz, 1H), 7.19-7.23 (m, 2H), 7.44 (dd, J = 4.4 and 9.0 Hz, 1H), 7.65 (dd, J= 2.6 and 9.6 Hz, 1H), 7.74 (d, J = 7.7 Hz, 3H), 8.18 (s, 1H) ppm. 13C NMR (75.5 MHz, CD3OD-DMSO-d6): delta = 21.3, 4.3, 106.9 (d, J = 25.1 Hz), 111.9 (d, J = 26.6 Hz), 112.3, 112.8, 114.0 (d, J = 9.8 Hz), 121.2, 121.4, 121.5, 124.6, 126.2, 127.5, 134.7, 134.9, 135.1, 160.0 (d, J= 235.1 Hz), 168.8, 175.5 ppm. LRMS (ESI): m/z = 422 and 424 [(M+Na)+].
50%	With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20℃;	To a stirred solution of indolic amine (gb) (72 mg, 0.3 mmol) and 5-fluoro-lH-indole-3- carboxylic acid (2f) (59 mg, 0.33 mmol) in 5 mL of dry CH2CI2, l-ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDCI, 5 mg, 0.33 mmol) was added at room temperature. The resulting mixture was stirred overnight. Then CH2CI2 was evaporated then EtOAc (20 mL) and a 1M aqueous solution of hydrochloric acid (20 mL) were added. After extraction, organic phase was washed with an aqueous solution of hydrochloric acid, a 5% aqueous solution of Na2C03, brine, dried over anhydrous MgSC>4, filtered, and concentrated under vacuum. Purification of the crude product by column chromatography using EtOAc-pentane (from 1/9 to 8/2) yielded the pure bis-indole 5 (60 mg, 0.226 mmol) as a beige foam. Yield: 50%.IR (neat): 3455, 3240, 2975, 2870, 1740, 1595, 1530, 1460, 1425, 1205, 1170, 1080, 1005, 930, 850, 760 cm"1. 1H NMR (300 MHz, CD3OD-DMSO-d6): delta = 1.60 (d, J= 6.8 Hz, 3H), 5.49 (q, J = 6.8 Hz, 1H), 6.99 (dt, J= 2.6 and 9.0 Hz, 1H), 7.09 (dd, J = 1.9 and 8.7 Hz, 1H), 7.19-7.23 (m, 2H), 7.44 (dd, J= 4.4 and 9.0 Hz, 1H), 7.65 (dd, J= 2.6 and 9.6 Hz, 1H), 7.74 (d, J= 7.7 Hz, 3H), 8.18 (s, 1H) ppm. 13C NMR (75.5 MHz, CD3OD-DMSO-d6): delta = 21.3, 4.3, 106.9 (d, J = 25.1 Hz), 1 11.9 (d, J = 26.6 Hz), 112.3, 112.8, 114.0 (d, J = 9.8 Hz), 121.2, 121.4, 121.5, 124.6, 126.2, 127.5, 134.7, 134.9, 135.1, 160.0 (d, J = 235.1 Hz), 168.8, 175.5 ppm. LRMS (ESI): m/z = 422 and 424 [(M+Na)+].

References: [1]Patent: EP2548864,2013,A1 .Location in patent: Paragraph 0315.
[2]Patent: WO2013/14102,2013,A1 .Location in patent: Page/Page column 58; 63; 64.

9
[ 1260793-83-6 ]
[ 23077-43-2 ]

Yield	Reaction Conditions	Operation in experiment
84%		1-(5-Fluoro-1H-indol-3-yl)-2,2,2-trifluoroethanone (hf) (693 mg, 3.0 mmol) was suspended in 10 mL of a 4M aqueous solution of sodium hydroxide. The resulting mixture was stirred at reflux during 1 hour. The solution was extracted with diethyl ether (2x25 mL) and then aqueous the phase was acidified with an aqueous solution of 5M HCl to pH 1. The precipitate was filtered off, washed with water and dried in the presence of P2O5 under reduced pressure. Pure 5-fluoroindolic acid (2e) (451 mg, 2.52 mmol) was obtained as a beige solid. Yield: 84%. 1H NMR (300 MHz, CD3OD): delta = 6.96 (td, J = 2.6 and 9.3 Hz, 1H), 7.40 (dd, J = 4.4 and 8.9 Hz, 1H), 7.71 (dd, J = 2.6 and 9.9 Hz, 1H), 7.98 (s, 1H), 11.41 (br s, 1H, NH) ppm. 13C NMR (75.5 MHz, CD3OD): delta = 106.9 (d, J = 25.1Hz, (CH)), 111.9 (d, J = 26.6 Hz, CH)), 114.0 (d, J = 9.8 Hz, (CH), 126.2 (C), 134.7 (C), 134.9 (CH), 160.0 (d, J = 235.1Hz, C), 168.8 (C), 175.5 (CO) ppm.
84%		Its synthesis from 1-(5-fluoro-1H-indol-3-yl)-2,2,2-trifluoroethanone (hf) was described in the following patent: T. C. Hancox et al., PCT Int. AppL, 2009053715, 30 Apr 2009. l-(5-Fluoro-lH-indol-3-yl)-2,2,2-trifluoroethanone (hf) (693 mg, 3.0 mmol) was suspended in 10 mL of a 4M aqueous solution of sodium hydroxide. The resulting mixture was stirred at reflux during 1 hour. The solution was extracted with diethyl ether (2x25 mL) and then aqueous the phase was acidified with an aqueous solution of 5M HCl to pH 1. The precipitate was filtered off, washed with water and dried in the presence of P2O5 under reduced pressure. Pure 5- fluoroindolic acid (2e) (451 mg, 2.52 mmol) was obtained as a beige solid. Yield: 84%.1H NMR (300 MHz, CD3OD): delta = 6.96 (td, J= 2.6 and 9.3 Hz, 1H), 7.40 (dd, J= 4.4 and 8.9 Hz, 1H), 7.71 (dd, J = 2.6 and 9.9 Hz, 1H), 7.98 (s, 1H), 11.41 (br s, 1H, NH) ppm. 13C NMR (75.5 MHz, CD3OD): delta = 106.9 (d, J = 25.1 Hz, (CH)), 111.9 (d, J = 26.6 Hz, CH)), 114.0 (d, J = 9.8 Hz, (CH), 126.2 (C), 134.7 (C), 134.9 (CH), 160.0 (d, J = 235.1 Hz, C), 168.8 (C), 175.5 (CO) ppm.
785 mg	With sodium hydroxide; In water; for 1.5h;Reflux;	2,2,2 trifluoro-1-[5-fluoro-l- (pyrimidin-2-yl)-1H-indol-3-yl] ethan-1-one(1.6 g)Was added 5 N sodium hydroxide aqueous solution (20 mL)And the mixture was stirred under heating reflux for 1.5 hours.After cooling the reaction solution to room temperature, water and ethyl acetate were added,And extracted with ethyl acetate. The obtained aqueous layer was made acidic with concentrated hydrochloric acid,The mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over sodium sulfate and the solvent was distilled off under reduced pressure to give 5-fluoro-lH-indole-3-carboxylic acid785 mg (yield 88%) was obtained.

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316.
[2]Patent: EP2548864,2013,A1 .Location in patent: Paragraph 0178; 0179.
[3]Patent: WO2013/14102,2013,A1 .Location in patent: Page/Page column 26; 32; 33.
[4]Patent: JP2017/171619,2017,A .Location in patent: Paragraph 0168; 0170.

10
[ 2338-71-8 ]
[ 23077-43-2 ]

References: [1]CrystEngComm,2013,vol. 15,p. 7490 - 7497.

11
5-fluoro-1H-indole-3-carbonitrile [ No CAS ]
[ 23077-43-2 ]

References: [1]CrystEngComm,2013,vol. 15,p. 7490 - 7497.

12
[ 1110273-51-2 ]
[ 23077-43-2 ]

References: [1]CrystEngComm,2013,vol. 15,p. 7490 - 7497.

13
[ 23077-43-2 ]
[ 74-88-4 ]
[ 310886-98-7 ]