[ CAS No. 773136-66-6 ] {[proInfo.proName]}

Name: 773136-66-6|Ethyl 2-Fluoro-5-iodobenzoate|95%
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Quality Control of [ 773136-66-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 773136-66-6 ]

SDS Specification

Alternatived Products of [ 773136-66-6 ]

Product Details of [ 773136-66-6 ]

CAS No. :	773136-66-6	MDL No. :	MFCD06204769
Formula :	C₉H₈FIO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GHRYAGFJSZGCAQ-UHFFFAOYSA-N
M.W :	294.06	Pubchem ID :	24820419
Synonyms :

Calculated chemistry of [ 773136-66-6 ]

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 :	55.2
TPSA :	26.3 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) :	-6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.25
Log Po/w (XLOGP3) :	2.89
Log Po/w (WLOGP) :	3.03
Log Po/w (MLOGP) :	3.52
Log Po/w (SILICOS-IT) :	3.43
Consensus Log Po/w :	3.02

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.63
Solubility :	0.0693 mg/ml ; 0.000236 mol/l
Class :	Soluble
Log S (Ali) :	-3.1
Solubility :	0.232 mg/ml ; 0.00079 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.1
Solubility :	0.0234 mg/ml ; 0.0000794 mol/l
Class :	Moderately soluble

Medicinal Chemistry

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

Safety of [ 773136-66-6 ]

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 [ 773136-66-6 ]

* 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 [ 773136-66-6 ]
Downstream synthetic route of [ 773136-66-6 ]

[ 773136-66-6 ] Synthesis Path-Upstream 1~1

1
[ 64-17-5 ]
[ 124700-41-0 ]
[ 773136-66-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	at 100℃; Inert atmosphere	Example 91N,N-Dibutyl-4-chloro- 1 -(2-((5)-3-(hydroxymethyl)- 1 ,2,3 ,4-tetrahydroisoquinoline-2- carbonyl)-4-(naphthalen-2-ylsulfonylcarbamoyl)phenyl)-5-methyl-lH-pyrazole-3- carboxamideIntermediate 91 A: Ethyl 2-fluo -5-iodobenzoate[00316] To a solution of 2-fluoro-5-iodobenzoic acid (Oakwood, 0.99 g, 3.72 mmol) in EtOH (7.4 mL) was added H₂S0₄ (198 μ, 3.72 mmol). The resulting reaction mixture was stirred at 100 °C overnight and then concentrated in vacuo. The crude oil was purified using flash column chromatography (gradient from 0percent to 10percent EtOAc/hexanes) to give the title compound (916 mg, 84percent) as a colorless oil. ^XH NMR (CDC1₃) δ 8.24 (dd, J= 6.8, 2.4 Hz, 1H), 7.81 (ddd, J= 8.8, 4.5, 2.4 Hz, 1H), 6.93 (dd, J= 10.3, 8.6 Hz, 1H), 4.41 (q, J= 7.0 Hz, 2H), 1.42 (t, J= 7.2 Hz, 3H).

Reference： [1] Patent: WO2012/162365, 2012, A1, . Location in patent: Page/Page column 173-174

[ 773136-66-6 ] Synthesis Path-Downstream 1~11

1
[ 64-17-5 ]
[ 124700-41-0 ]
[ 773136-66-6 ]

Yield	Reaction Conditions	Operation in experiment
94.9%	With sulfuric acid; at 100℃; for 5h;	Compound 1 (20.0 g, 75.2 mmol, 1 eq) was dissolved in 70 mL of EtOH.Then gradually add H2SO4 (7.37g, 75.1mmol, 4.01mL, 1eq).The mixture was stirred at 100 C for 5 h.And use TLC (Dichloromethane/Methanol=10/1, Rf=0.87) The progress of the reaction was detected.When the reaction is complete,The reactants were concentrated under reduced pressure.The concentrated product was extracted (EOtOH 200 mL, NaHCO 3 saturated solution (100.0 mL x 2), and then the organic layer was taken.It was dried by adding anhydrous Na2SO4.After further evaporation to dryness the title product 2 (21.0 g, 71.4 mmol, 94.9% yield).Figure 3 shows the results of TLC chromatography for this reaction.
84%	With sulfuric acid; at 100℃;Inert atmosphere;	Example 91N,N-Dibutyl-4-chloro- 1 -(2-((5)-3-(hydroxymethyl)- 1 ,2,3 ,4-tetrahydroisoquinoline-2- carbonyl)-4-(naphthalen-2-ylsulfonylcarbamoyl)phenyl)-5-methyl-lH-pyrazole-3- carboxamideIntermediate 91 A: Ethyl 2-fluo -5-iodobenzoate[00316] To a solution of <strong>[124700-41-0]2-fluoro-5-iodobenzoic acid</strong> (Oakwood, 0.99 g, 3.72 mmol) in EtOH (7.4 mL) was added H2S04 (198 mu, 3.72 mmol). The resulting reaction mixture was stirred at 100 C overnight and then concentrated in vacuo. The crude oil was purified using flash column chromatography (gradient from 0% to 10% EtOAc/hexanes) to give the title compound (916 mg, 84%) as a colorless oil. XH NMR (CDC13) delta 8.24 (dd, J= 6.8, 2.4 Hz, 1H), 7.81 (ddd, J= 8.8, 4.5, 2.4 Hz, 1H), 6.93 (dd, J= 10.3, 8.6 Hz, 1H), 4.41 (q, J= 7.0 Hz, 2H), 1.42 (t, J= 7.2 Hz, 3H).

Reference： [1]Patent: CN109942582,2019,A .Location in patent: Paragraph 0057-0061
[2]Patent: WO2012/162365,2012,A1 .Location in patent: Page/Page column 173-174

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid;Reflux;	General procedure: Intermediate 3: .0 To a mixture of commercially available 2-chloro-5-hydroxybenzoic acid (4 g, 23.18mmol) in dry EtOH ( 90 mL), concentrated sulphuric acid (1 mL, 17.62mmol) was added. The mixture was stirred under reflux overnight, then solvent evaporated under reduced pressure and the residue dissolved with DCM. A saturated solution of NaHCO3 was added, phases were separated, organics dried over sodium sulphate , filtered and evaporated to obtain 5 g of the corresponding 2-chloro-5-hydroxy- benzoic acid ethyl ester. HPLC-MS (Method 2): Rt = 1 .0 min MS: m/z = 201 .6 (M+H)+
	With sulfuric acid;Reflux;	General procedure: To a mixture of commercially available 2-chloro-5- hydroxybenzoic acid (4 g, 23.18 mmol) in dry EtOR (90 mE), concentrated sulphuric acid (1 mE, 17.62 mmol) was added. The mixture was stirred under reflux overnight, then solvent evaporated under reduced pressure and the residue dissolved with DCM. A saturated solution of NaHCO3 was added, phases were separated, organics dried over sodium sulphate, filtered and evaporated to obtain 5 g of the corresponding 2-chioro-5-hydroxybenzoic acid ethyl ester.10567] HPEC-MS (Method 2): R=1 .0 mm10568] MS: mlz=201.6 (M+H7

3
[ 1191-95-3 ]
[ 773136-66-6 ]
[ 1552285-72-9 ]

Yield	Reaction Conditions	Operation in experiment
3 g		Under nitrogen atmosphere, starting Ester Intermediate 5e (5.0 g, 15.3 mmol) was dissolved in THF (40 mL), the reaction mixture was cooled to -50C and stirred for 10 minutes. Isopropyl-magnesium-chloride (1 1 mL of a 2M solution in THF) was added dropwise and the reaction mixture was stirred at -50C for 2h. The reaction mixture was cooled to -78C and a solution of cyclobutanone (2.15 g, 30.6 mmol) in THF (10 mL) was added dropwise. The reaction mixture was stirred at -78C for 1 h, then warmed to room temperature and stirred for 18h. The solvent was removed under vacuum, dichloromethane was added and the reaction mixture was washed with a saturated solution of NaHCO3, The organic phase was concentrated under vacuum and the crude product obtained was purified by flash chromatography (eluent from 90:10 to 80:20 Cy/EtOAc) to obtain the desired product (3.0 g). GC-MS (Method 10): Rt = 10.91 min MS : m/z = 210 (M-28)+
3 g		10586] Under nitrogen atmosphere, starting Ester Intermediate Se (5.0 g, 15.3 mmol) was dissolved inTHF (40 mE), the reaction mixture was cooled to -50 C. and stirred for 10 minutes. Isopropyl-magnesium-chioride (11 mE of a 2M solution in THF) was added dropwise and the reaction mixture was stirred at -50 C. for 2 h. The reaction mixture was cooled to -78 C. and a solution of cyclobutanone (2.15 g, 30.6 mmol) in THF (10 mE) was added dropwise. The reaction mixture was stirred at -78 C. for 1 h, then warmed to room temperature and stirred for 18 h. The solvent was removed under vacuum, dichloromethane was added and the reaction mixture was washed with a saturated solution of NaHCO3, The organic phase was concentrated under vacuum and the crude product obtained was purified by flash chromatography (eluent from 90:10 to 80:20 Cy/EtOAc) to obtainthe desired product (3.0 g).10587] GC-MS (Method 10): R=10.91 mm10588] MS: mlz=210 (M-28)

Reference： [1]Patent: WO2014/19979,2014,A1 .Location in patent: Page/Page column 99
[2]Patent: US2014/45856,2014,A1 .Location in patent: Paragraph 0585-0588

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[ 773136-66-6 ]
2-(2-fluoro-5-iodophenyl)pyrrolidine [ No CAS ]