[ CAS No. 769965-95-9 ]

Name: 769965-95-9|5'-Fluorospiro[cyclopropane-1,3'-indolin]-2'-one|98%
Brand: Ambeed
SKU: A186758
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3d Animation Molecule Structure of 769965-95-9

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Quality Control of [ 769965-95-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 769965-95-9 ]

SDS Specification

Alternatived Products of [ 769965-95-9 ]

Product Details of [ 769965-95-9 ]

CAS No. :	769965-95-9	MDL No. :	MFCD13195329
Formula :	C₁₀H₈FNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KTOQUUHQTKCDEM-UHFFFAOYSA-N
M.W :	177.18 g/mol	Pubchem ID :	58398965
Synonyms :

Calculated chemistry of [ 769965-95-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	49.08
TPSA :	29.1 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.82
Log Po/w (XLOGP3) :	1.22
Log Po/w (WLOGP) :	1.6
Log Po/w (MLOGP) :	2.17
Log Po/w (SILICOS-IT) :	2.73
Consensus Log Po/w :	1.91

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.05
Solubility :	1.58 mg/ml ; 0.00894 mol/l
Class :	Soluble
Log S (Ali) :	-1.43
Solubility :	6.61 mg/ml ; 0.0373 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.71
Solubility :	0.0349 mg/ml ; 0.000197 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 769965-95-9 ]

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 [ 769965-95-9 ]

* 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 [ 769965-95-9 ]

[ 769965-95-9 ] Synthesis Path-Downstream 1~10

1
[ 769965-95-9 ]
5’-fluorospiro[cyclopropane-1,3’-indoline] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; at 0 - 50℃; for 3.25h;	A sample of <strong>[769965-95-9]5-fluoro-siprocyclopropyloxindole</strong> (172 mg, 97 jimol) was cooled in an ice/water bath and treated with a 1.0 M solution of LAH (1.94 ml, 1.9 mmol). The reaction was stirred at room temperature for 15 minutes and then at 50 C for 3 hours and finally was cooled back down with an icelwater bath. The reaction was treated with 1 M NaOH (1.9 mL) followed by water (1.9 mL). The reaction was filtered over celite and dried over MgS04. After filtration, the solvent was removed and the crude material of 5-fluoro- siprocyclopropylindoline was used without purification.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 50℃; for 3h;	A sample of <strong>[769965-95-9]5-fluoro-siprocyclopropyloxindole</strong> (172 mg, 97 NMOL) was cooled in an ice/water bath and treated with a 1.0 M solution of LAH (1.94 ml, 1.9 mmol). The reaction was stirred at room temperature for 15 minutes and then at 50 C for 3 hours and finally was cooled back down with an ICE/WATER bath. The reaction was treated with 1 M NAOH (1.9 mL) followed by water (1.9 mL). The reaction was filtered over celite and dried over MGS04. After filtration, the solvent was removed and the crude material of 5-fluoro- siprocyclopropylindoline was used without purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5107 - 5111
[2]Patent: WO2005/34848,2005,A2 .Location in patent: Page/Page column 45
[3]Patent: WO2005/18568,2005,A2 .Location in patent: Page/Page column 37

2
[ 769965-94-8 ]
[ 769965-95-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With trifluoroacetic acid; at 60℃;	A solution of 5-fluoro-1-(4-methoxy-benzyl)-siprocyclopropyloxindole (3. 38 g, 11.4 mmol) in TFA (20 mL) was stirred at 60 C overnight. The solvent was then removed and the reaction was diluted with ethyl acetate and washed with saturated aqueous NaHCO3 until the washings were neutral. The organic phase was then washe with brine, dried over Na2S04 and the solvent was removed. The residue was purified by silica gel chromatography using a gradient of 0-100% ethyl acetate in hexane to afford 1.94 g (96%) of 5-fluoro-siprocyclopropyloxindole ; 1H NMR (MeOD, 400 MHz) os 1. 76-1.86 (m, 4H), 6.91- 6.94 (m, 1H), 7.07-7. 11 (m, 2H); HPLC-MS calcd. for CloHsFNO (M +H 178.2, found 178.3.
96%	With trifluoroacetic acid; at 60℃;	A solution of 5-fluoro-1-(4-methoxy-benzyl)-siprocyclopropyloxindole (3.38 g, 11.4 mmol) in TFA (20 mL) was stirred at 60 C overnight. The solvent was then removed and the reaction was diluted with ethyl acetate and washed with saturated aqueous NAHCO3 until the washings were neutral. The organic phase was then washed with brine, dried over Na2SO4 and the solvent was removed. The residue was purified by silica gel chromatography using a gradient of 0-100% ethyl acetate in hexane to afford 1.94 g (96%) of 5-FLUOR- siprocyclopropyloxindole

Reference： [1]Patent: WO2005/34848,2005,A2 .Location in patent: Page/Page column 44-45
[2]Patent: WO2005/18568,2005,A2 .Location in patent: Page/Page column 36
[3]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5107 - 5111

3
[ 769965-93-7 ]
[ 769965-95-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5107 - 5111
[2]Patent: WO2005/34848,2005,A2
[3]Patent: WO2005/18568,2005,A2

4
[ 443-69-6 ]
[ 769965-95-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5107 - 5111
[2]Patent: WO2005/34848,2005,A2
[3]Patent: WO2005/18568,2005,A2

5
[ 522612-15-3 ]
[ 769965-95-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5107 - 5111
[2]Patent: WO2005/34848,2005,A2
[3]Patent: WO2005/18568,2005,A2

6
[ 56341-41-4 ]
[ 106-93-4 ]
[ 769965-95-9 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate H5'-F I uorospiro[cyc I op ropane-1 3'-i ndol i n]-2'-one5-Fluoroindolin-2-one (500 mg, 3.31 mmol) was dissolved in dry THF (30 ml). To this was added N1 ,N1,N2,N2-tetramethylethane-1,2-diamine (1.091 ml, 7.28 mmol) and the mixture was cooled to -78C. BuLi (1.6M in Hexanes) (4.14 ml, 6.62 mmol) was added dropwise and the contents left stirring for 20 mins. 1 ,2-Dibromoethane (0.342 ml, 3.97 mmol) was added dropwise and the mixture was stirred at -78C for 30 mins and allowed to warm to RT overnight. The reaction was quenched by addition of NH CI (20 ml) and extracted into EtOAc. The solvent was removed in vacuo and purification by chromatography on silica eluting with acetone/iso-hexane afforded the title compound as a white solid; 1H NMR (400 MHz, CDCI3) delta 8.40 (1H, s), 6.90 (2H, m), 6.60 (1 H, d), 1.80 (2H, m), 1.55 (2H, m).

Reference： [1]Patent: WO2011/92293,2011,A1 .Location in patent: Page/Page column 85

7
[ 769965-95-9 ]
[ 1319743-48-0 ]
[ 1319742-72-7 ]

Yield	Reaction Conditions	Operation in experiment
		Example 2.5Trans-2-chloro-N-{-4-((5'-fluoro-2'-oxospiro[cyclopropane-1 ,3'-indoline]-1 yl)methyl)cyctohexyl}-5-(trifluoromethyl)benzamide 5'-Fluorospiro[cyclopropane-1 ,3'-indolin]-2'-one (Intermediate H) {67 mg, 0.378 mmol) in dry D F (3 ml) was treated with NaH {60% in mineral oil) (15.12 mg, 0.378 mmol) under N2 and the contents left stirring for ~10 mins. After this time, trans- methanesulfonic acid 4-{2-chloro-5-trifluoromethyl-benzoylamino)-cyclohexyl methyl ester (Intermediate C) (105 mg, 0.253 mmol) was added and the solution heated to 70C for 2.5 h. After cooling to RT overnight, the mixture was diluted with EtOAc/H20 (40 ml) and transferred to a separating funnel. The organic layer was separated and washed with brine, dried (MgS04), and concentrated in vacuo to give a light brown oil. The crude oil was chromatographed on silica eluting with a gradient of 0%-30% EtOAc/iso-hexane follwed by an isocratic gradient of 30% EtOAc/iso-hexane to afford the title compound as a white solid; LC-MS Rt= 1.36 mins; [M+H]+ 495.3; Method = 2minl_C_30_v002. 1H NMR (400 MHz, CDCI3). delta 7.90 (1H, s), 7.55 (1 H, d), 7.50 (1H, d), 6.95 (1H, m), 6.80 (1 H, m), 6.60 (1H, m), 5.95 (1 H, d), 4.0 (1H, m), 3.65 (2H, d), 2.20 (2H, m), 1.85 (5H, m), 1.55 (2H, m), 1.25 (4H, m).

Reference： [1]Patent: WO2011/92293,2011,A1 .Location in patent: Page/Page column 48-49

8
[ 769965-95-9 ]
{5-chloro-1-[2-(methylsulfonyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-2-yl}methyl methanesulfonate [ No CAS ]
1'-({5-chloro-1-[2-(methylsulfonyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-2-yl}methyl)-5'-fluorospiro[cyclopropane-1,3'-indol]-2'(1'H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 0.5h;	A mixture of {5-chloro-1-[2-(methylsulfonyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-2-yl}methyl methanesulfonate (183 mg, 0.50 mmol), cesium carbonate (325 mg, 1.0 mmol) and <strong>[769965-95-9]5'-fluorospiro[cyclopropane-1,3'-indol]-2'(1'H)-one</strong> (79 mg, 0.50 mmol) in N,N-dimethylformamide (5 mL) was heated with stirring at 60C for 30 minutes. The resulting mixture was purified by preparative HPLC to afford the title product.

Reference： [1]Patent: WO2014/184163,2014,A1 .Location in patent: Page/Page column 112

9
[ 56341-41-4 ]
diphenyl(vinyl)sulfonium trifluoromethanesulfonate [ No CAS ]
[ 769965-95-9 ]

Reference： [1]RSC Advances,2017,vol. 7,p. 3741 - 3745

10
[ 56341-41-4 ]
(2-bromoethyl)(diphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]
[ 769965-95-9 ]

Yield	Reaction Conditions	Operation in experiment
78%		General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3×30 mL). The combined organic layer washed with H2O (2×10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

Reference： [1]Tetrahedron,2018,vol. 74,p. 6809 - 6814

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Ghs Precautionary Statements

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P321
P322
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 769965-95-9 ]

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[ 769965-95-9 ] Synthesis Path-Downstream 1~10

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Fluorinated Building Blocks

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Indolines

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[ 769965-95-9 ]

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