[ CAS No. 884494-51-3 ] {[proInfo.proName]}

Name: 884494-51-3|2-Fluoro-4-iodonicotinic acid|95%
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SKU: A219811
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Quality Control of [ 884494-51-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 884494-51-3 ]

SDS Specification

Alternatived Products of [ 884494-51-3 ]

Product Details of [ 884494-51-3 ]

CAS No. :	884494-51-3	MDL No. :	MFCD03095310
Formula :	C₆H₃FINO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QKPLTGKHTYHYLU-UHFFFAOYSA-N
M.W :	267.00	Pubchem ID :	44754754
Synonyms :

Calculated chemistry of [ 884494-51-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.87
TPSA :	50.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.2
Log Po/w (XLOGP3) :	1.46
Log Po/w (WLOGP) :	1.94
Log Po/w (MLOGP) :	0.25
Log Po/w (SILICOS-IT) :	2.15
Consensus Log Po/w :	1.4

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.75
Solubility :	0.472 mg/ml ; 0.00177 mol/l
Class :	Soluble
Log S (Ali) :	-2.12
Solubility :	2.02 mg/ml ; 0.00758 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.63
Solubility :	0.627 mg/ml ; 0.00235 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.79

Safety of [ 884494-51-3 ]

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

Application In Synthesis of [ 884494-51-3 ]

* 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 [ 884494-51-3 ]
Downstream synthetic route of [ 884494-51-3 ]

[ 884494-51-3 ] Synthesis Path-Upstream 1~3

1
[ 153034-82-3 ]
[ 884494-51-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In water; <i>tert</i>-butyl alcohol at 20℃; for 1.25 h;	To a stirred solution of 2-fluoro-4-iodopyridine-3- carboxaldehyde (10.Og₅ 39.8 rnmol) in tert-butanol (350 mL) and water (100 niL) at room temperature were added 2-methyl-2-butene (42.1 ml, 398 mmol), sodium phosphate, monobasic, monohydrate (60.5 g, 438 mmol) and sodium chlorite (18.0 g, 199 mmol). The reaction mixture was stirred at room temperature for 75 min. The reaction mixture was diluted with dichloromethane and a 6M aqueous solution of hydrochloric acid was added until pH ~2. EPO <DP n="196"/>T/US2006/016344The water layer was extracted with dichloromethane. The organic phase was dried over MgSO₄, filtered and concentrated in vacuo. Purification by MPLC (CH₂Cl₂MeOH+ 1percent AcOH: 100/0 to 80/20) afforded 2-fluoro-4-iodonicotinic acid (10.63 g, 39.8 mmol, 100percent yield). MS (ESI pos. ion) m/z: 268 (MH+). Calc'd exact mass for C₆H₃FINO₂: 267.

Reference： [1] Patent: WO2006/116713, 2006, A1, . Location in patent: Page/Page column 194-195
[2] Patent: WO2016/95204, 2016, A1, . Location in patent: Page/Page column 62; 63

2
[ 372-48-5 ]
[ 884494-51-3 ]

Reference： [1] Patent: WO2016/95204, 2016, A1,

3
[ 884494-51-3 ]
[ 18107-18-1 ]
[ 884494-84-2 ]

Yield	Reaction Conditions	Operation in experiment
5.3 g	at 10 - 35℃; for 3 h; Inert atmosphere	To a solution of 2-fluoro-4-iodonicotinic acid (5.13 g) in diethyl ether (25 mL)-methanol (25 mL) was added 10percent trimethylsilyldiazomethane (hexane solution) (32.9 g), and the mixture was stirred under a nitrogen atmosphere at room temperature for 3 hr. The reaction solution was concentrated, and the residue was purified by silica gel chromatography (hexane-ethyl acetate) to give the title compound (5.3 g). ¹H NMR (300 MHz, DMSO-d₆) δ 3.94 (3H, s), 7.98 (1H, dd, J = 5.3, 1.1 Hz), 8.07 (1H, dd, J = 5.3, 0.8 Hz).

Reference： [1] Patent: EP2921480, 2015, A1, . Location in patent: Paragraph 0391; 0392
[2] Patent: WO2016/95204, 2016, A1, . Location in patent: Page/Page column 62; 63

[ 884494-51-3 ] Synthesis Path-Downstream 1~82

1
[ 884494-51-3 ]
[ 726206-61-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogenchloride; water; at 100℃; for 1.08333h;	A suspension of <strong>[884494-51-3]2-fluoro-4-iodonicotinic acid</strong> (896 mg, 3356 mumol) in 6M hydrochloric acid (13423 mul, 80540 mumol) was heated at 100 0C. After 5 min, the reaction became a solution, and then a precipitate appeared. The reaction mixture was stirred 60 min at 100 0C and then cooled to room temperature. Filtration afforded 2- hydroxy-4-iodonicotinic acid (710 mg, 2679 mumol, 80% yield). MS (ESI pos. ion) m/z: 248(M+H-H2O). Calc'd exact mass for C6H4INO3: 265.

Reference： [1]Patent: WO2006/116713,2006,A1 .Location in patent: Page/Page column 194-195

2
[ 153034-82-3 ]
[ 884494-51-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20℃; for 1.25h;	To a stirred solution of 2-fluoro-4-iodopyridine-3- carboxaldehyde (10.Og5 39.8 rnmol) in tert-butanol (350 mL) and water (100 niL) at room temperature were added 2-methyl-2-butene (42.1 ml, 398 mmol), sodium phosphate, monobasic, monohydrate (60.5 g, 438 mmol) and sodium chlorite (18.0 g, 199 mmol). The reaction mixture was stirred at room temperature for 75 min. The reaction mixture was diluted with dichloromethane and a 6M aqueous solution of hydrochloric acid was added until pH ~2. EPO <DP n="196"/>T/US2006/016344The water layer was extracted with dichloromethane. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. Purification by MPLC (CH2Cl2MeOH+ 1% AcOH: 100/0 to 80/20) afforded 2-fluoro-4-iodonicotinic acid (10.63 g, 39.8 mmol, 100% yield). MS (ESI pos. ion) m/z: 268 (MH+). Calc'd exact mass for C6H3FINO2: 267.
81%	With sodium chlorite; disodium hydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 25℃; for 1.5h;	To a solution of 401-B (13.3 g, 53 mmol) in 466 mL of t-BuOH and 133 mL of water cooled with ice-eater wasadded 2-Methyl-2-butene (13.3 g, 53 mmol), Na2HPO4 (70 g, 583 mmol), followed by NaClO2 (24g, 265 mmol) portionwise.The reaction mixture was stirred at 25 C for 1.5 hours, then diluted with 800 mL of DCM and acidified with 6 N/HClto pH = 2. The organic phase was separated and the water phase was extracted with DCM/MeOH (20:1, 1000 mL2).The combined organic phase was washed with brine, dried over Na2SO4. Filtered and concentrated to dry. The residuewas crystallized from DCM/PE(1:1) to give product 401-C (2-fluoro-4-iodonicotinic acid, 11.5g, yield: 81%).1H NMR (300 MHz, DMSO-d6): delta 14.26 (br s, 1H), 8.02 (d, J = 4.2 Hz, 1H), 7.94 (dd, J = 3.9, 0.6 Hz, 1H).
	With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20℃; for 16h;	To a mixture of the product from step I (25 g, 99.6 mmol) in t-BuOH/water (240/80 mL) at IT was added 2-methyi-2-butene (105 mI), NaC1O2 (45g, 498 mmol) and NaH2PO4 (120 mg, 100 mnioi) and the resulting mixture stirred at RI? for i6h. Saturated aq. Na2503 wasadded, the mixture acidified to pH 34 with 2M HCI and the mixture extracted with EtOAc (200 ml. x 3). The combined organic layers were dried over Na2504, filtered, the filtrate concentrated in vacuo to give the title compound as an oil, which was used in the next step directly. LRMS mz (M+i-{) 268.1 found, 268.1 required.

Reference： [1]Patent: WO2006/116713,2006,A1 .Location in patent: Page/Page column 194-195
[2]Patent: EP3590924,2020,A1 .Location in patent: Paragraph 0172; 0177
[3]Patent: WO2016/95204,2016,A1 .Location in patent: Page/Page column 62; 63

3
[ 884494-51-3 ]
[ 1431473-05-0 ]
C₁₇H₂₃IN₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1 : Methyl 2-(((3R.6R)-l-(ter?-butoxycarbonyl)-6-methylpiperidin-3-yl)oxy)-4- iodonicotinate A solution of <strong>[884494-51-3]2-fluoro-4-iodonicotinic acid</strong> (4.43 g, 16.61 mmol) in DMSO (75 ml) was treated with sodium hydride (0.471 g, 19.62 mmol) in portions. After stirring a few minutes, (2R,5R)-tert-butyl 5-hydroxy-2-methylpiperidine-l-carboxylate (8, 3.25 g, 15.10 mmol) was added. Additional sodium hydride (0.362 g, 15.10 mmol) was added in portions and, after stirring for a few minutes, the reaction was heated at 40 C for 2 days. The reaction was cooled and quenched with saturated, aqu. NH4C1, then rapidly diluted with H2O and EtOAc. Cone. HCl was added until the the solution was acidic, then rapidly extracted 3x with EtOAc. The organics were washed 2x with H20, lx with brine, dried over MgS04, filtered, concentrated, and dried to provide the crude carboxylic acid. The crude foam was dissolved in DMF (76 mL) and cooled at 0 C and treated with sodium hydride (0.55 g, 23 mmol) in portions. After stirring ~10 mins, iodomethane (1.34 mL, 21.4 mmol) was added and the reaction was warmed to RT overnight. The reaction was cooled at 0 C and quenched by additon of saturated, aqu. NH4C1 and stirred well. Saturated, aqu. aHC03 was added and the reaction was extracted 2x with EtOAc. The organic fractions were washed with brine, dried over MgS04, filtered, and concentrated to provide the title compound as a crude oil. LRMS m/z (M+H) 477.3 found, 477.1 required.

Reference： [1]Patent: WO2014/62533,2014,A1 .Location in patent: Page/Page column 37-38

4
[ 884494-51-3 ]
[ 1431473-05-0 ]
C₁₇H₂₂IN₂O₅^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1: Methyl 2-(((3R,6R)-1-(tert-butoxycarbonyl)-6-methylpiperidin-3-yl)oxy)-4-iodonicotinate (15) A solution of <strong>[884494-51-3]2-fluoro-4-iodonicotinic acid</strong> (0.651 g, 2.44 mmol) in DMF (3 mL) was treated with sodium hydride (0.072 g, 3.0 mmol). After stirring ~5 minutes, tert-butyl (2R,5R)-5- hydroxy-2-methylpiperidine-1-carboxylate (Example 2, 8, 0.500 g, 2.32 mmol) and sodium hydride 10 (0.072 g, 3.0 mmol) were added, and the reaction was heated to 40 C for 1 hour. Iodomethane (0.73 mL, 0.012 mmol) was added, and the reaction was stirred at RT. After 1 hour, the mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography eluting with 0-20% ethyl acetate in hexanes to provide the title compound as a colorless oil. LRMS m/z (M+H) 477.2 found, 477.2 required.

Reference： [1]Patent: WO2015/88864,2015,A1 .Location in patent: Page/Page column 51

5
[ 884494-51-3 ]
methyl 4-iodo-2-((tetrahydrofuran-2-yl)methoxy)nicotinate [ No CAS ]