[ CAS No. 1337533-31-9 ] {[proInfo.proName]}

Name: 1337533-31-9|tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate|97%
Brand: Ambeed
SKU: A106075
Price: 34.0 USD
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Quality Control of [ 1337533-31-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1337533-31-9 ]

SDS Specification

Alternatived Products of [ 1337533-31-9 ]

Product Details of [ 1337533-31-9 ]

CAS No. :	1337533-31-9	MDL No. :	MFCD29760339
Formula :	C₁₃H₁₅BrFNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VRWHIDGFWSDQAY-UHFFFAOYSA-N
M.W :	316.17	Pubchem ID :	66823682
Synonyms :

Calculated chemistry of [ 1337533-31-9 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.46
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	75.03
TPSA :	29.54 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.38
Log Po/w (XLOGP3) :	3.5
Log Po/w (WLOGP) :	3.93
Log Po/w (MLOGP) :	3.59
Log Po/w (SILICOS-IT) :	3.28
Consensus Log Po/w :	3.53

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.05
Solubility :	0.0279 mg/ml ; 0.0000883 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.8
Solubility :	0.0497 mg/ml ; 0.000157 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.3
Solubility :	0.016 mg/ml ; 0.0000505 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.58

Safety of [ 1337533-31-9 ]

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 [ 1337533-31-9 ]

* 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.

Upstream synthesis route of [ 1337533-31-9 ]
Downstream synthetic route of [ 1337533-31-9 ]

[ 1337533-31-9 ] Synthesis Path-Upstream 1~1

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[ 1337533-31-9 ]
[ 1337532-29-2 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 10, p. 964 - 968

[ 1337533-31-9 ] Synthesis Path-Downstream 1~22

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[ 73183-34-3 ]
[ 1337533-32-0 ]

Yield	Reaction Conditions	Operation in experiment
57.4%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 100.0℃;	1.1 -dimethylethyl 4-fluoro-5-(4.4.5.5-tetrameth yl-1.3.2-dioxaborolan-2-yl)-2.3-dih vdro-1H- indole- 1-carboxylateA mixture of 1 , 1-dimethylethyl 5-bromo-4-fluoro-2,3-dihydro-1 H-indole-1-carboxylate (1 g, 3.16 mmol), PdCI2(dppf)-CH2CI2 adduct (0.129 g, 0.158 mmol), potassium acetate (0.776 g, 7.91 mmol) and bis(pinacolato)diboron (0.803 g, 3.16 mmol) in 1 ,4-Dioxane (20 mL) was stirred at 100 C overnight on a stirrer hot-plate. LCMS indicated complete conversion to the desired product. The reaction mixture was poured into 1 :1 NaCI(aq. sat.): H20, (100 mL) and ethyl acetate (100 mL), shaken, and filtered through celite. The resulting mixture was separated and the aqueous layer was extracted with two additional portions of ethyl acetate (2 x 50 ml_). The combined organics were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (0- 25% EtOAc in hexanes, 40 g silica gel column) to afford 1 ,1 -dimethylethyl 4-fluoro-5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H-indole-1-carboxylate (660 mg, 57.4 % yield) as a pale yellow oil. LC-MS(ES) m/z = 308 [M+H-tBu]+. 1H NMR (400 MHz, DMSO-d6) delta 1.29 (s, 12 H), 1 .51 (s, 9 H), 3.05 (t, J = 8.72 Hz, 2 H), 3.98 (t, J = 8.72 Hz, 2 H), 7.22 - 7.61 (m, 2 H).
57.4%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100.0℃;	1.1-dimethylethyl 4-fluoro-5-(4.4.5.5-tetramethyl-1.3.2-dioxaborolan-2-yl)-2.3-dihydro-1H-indole-1-carboxylateA mixture of 1 , 1-dimethylethyl 5-bromo-4-fluoro-2,3-dihydro-1 H-indole-1-carboxylate (1 g, 3.16 mmol), PdCI2(dppf)*CH2CI2 adduct (0.129 g, 0.158 mmol), potassium acetate (0.776 g, 7.91 mmol) and bis(pinacolato)diboron (0.803 g, 3.16 mmol) in 1 ,4-dioxane (20 ml_) was stirred at 100 C overnight on a stirrer hot-plate. LCMS indicated complete conversion to the desired product. The reaction mixture was poured into 1 : 1 saturated aqueous NaCI: H20 (100 ml_) and ethyl acetate (100 ml_), shaken, and filtered through celite. The resulting mixture was separated and the aqueous layer was extracted with two additional portions of ethyl acetate (2 x 50 ml_). The combined organics were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (0-25% EtOAc in hexanes, 40 g silica gel column) to afford 1 , 1- dimethylethyl 4-fluoro-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H- indole- 1-carboxylate (660 mg, 57.4 % yield) as a pale yellow oil. LC-MS(ES) m/z = 308 [M+H-tBu]+. H NMR (400 MHz, DMSO-d6) delta 1.29 (s, 12 H), 1.51 (s, 9 H), 3.05 (t, J = 8.72 Hz, 2 H), 3.98 (t, J = 8.72 Hz, 2 H), 7.22 - 7.61 (m, 2 H).

Reference： [1]Patent: WO2011/119663,2011,A1 .Location in patent: Page/Page column 188-189
[2]Patent: WO2015/56180,2015,A1 .Location in patent: Page/Page column 69

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[ 387-43-9 ]
[ 1337533-31-9 ]

Reference： [1]Patent: WO2011/119663,2011,A1
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 964 - 968
[3]Patent: WO2015/56180,2015,A1
[4]Patent: WO2016/86200,2016,A1

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[ 552866-98-5 ]
[ 1337533-31-9 ]

Reference： [1]Patent: WO2011/119663,2011,A1
[2]Patent: WO2015/56180,2015,A1
[3]Patent: WO2016/86200,2016,A1

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[ 1037075-45-8 ]
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Yield	Reaction Conditions	Operation in experiment
87%	With N-Bromosuccinimide; In dichloromethane;	1, 1-dimethylethyl 5-bromo-4-fluoro-2,3-dihydro-1H-indole-1-carboxylateTo a solution of 1 , 1-dimethylethyl 4-fluoro-2,3-dihydro-1 H-indole-1 -carboxylate (0.866 g, 3.65 mmol) in Dichloromethane (DCM) (10 mL) was added a solution of NBS (0.650 g, 3.65 mmol) in Dichloromethane (DCM) (10 mL). The reaction was stirred overnight. The reaction mixture was poured into sodium bicarbonate (aq., sat., 50 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (0-30% EtOAc in hexanes, 24-g silica gel column) to afford 1 ,1 -dimethylethyl 5-bromo-4-fluoro- 2,3-dihydro-1 H-indole-1-carboxylate ( 1 g, 87 % yield) as a (4:1 LCMS, 10:1 by 1 H NMR) mixture with the starting material. The mixture was used without further purification. LC- MS(ES) m/z = 260, 262 [M+H-t-Bu]+. 1 H NMR (400 MHz, DMSO-d6) delta 1.51 (s, 9 H), 3.13 (t, J = 8.72 Hz, 2 H), 3.94 - 4.08 (m, 2 H), 7.26 - 7.63 (m, 2 H).
75%	With N-Bromosuccinimide; In dichloromethane; at 20.0℃; for 2.0h;	To a solution of tert-butyl 4-fluoroindoline-l-carboxylate (3.0 g, 12.64 mmol) in DCM (30 mL) was added N-bromosuccinimide (3.4 g, 12.64 mmol). The mixture was stirred at 20 Cfor 2 h. The mixture was concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc = 9: 1) to give the title compound (3.0 g, 75%) as a brown oil.
1 g	With N-Bromosuccinimide; In dichloromethane;	1,1-dimethylethyl 5-bromo-4-fluoro-2, 3-dihydro-1H-indole-1-carboxylateTo a solution of 1 , 1-dimethylethyl 4-fluoro-2,3-dihydro-1 H-indole-1-carboxylate (0.866 g, 3.65 mmol) in dichloromethane (DCM) (10 mL) was added a solution of NBS (0.650 g, 3.65 mmol) in dichloromethane (DCM) (10 mL). The reaction was stirred overnight. The reaction mixture was poured into saturated aqueous sodium bicarbonate (50 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (0-30% EtOAc in hexanes, 24-g silica gel column) to afford 1 , 1- dimethylethyl 5-bromo-4-fluoro-2,3-dihydro-1 H-indole-1-carboxylate (1 g) as a (4: 1 LCMS, 10: 1 by H NMR) mixture with the starting material. The mixture was used without further purification. LC-MS(ES) m/z = 260, 262 [M+H-t-Bu]+. H NMR (400 MHz, DMSO-d6) delta 1.51 (s, 9 H), 3.13 (t, J = 8.72 Hz, 2 H), 3.94 - 4.08 (m, 2 H), 7.26 - 7.63 (m, 2 H).

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 964 - 968
[2]Patent: WO2011/119663,2011,A1 .Location in patent: Page/Page column 188
[3]Patent: WO2016/86200,2016,A1 .Location in patent: Page/Page column 344
[4]Patent: WO2015/56180,2015,A1 .Location in patent: Page/Page column 68

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[ 1337533-33-1 ]

Reference： [1]Patent: WO2011/119663,2011,A1
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 964 - 968

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[ 1337533-34-2 ]

Reference： [1]Patent: WO2011/119663,2011,A1

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[ 1337533-70-6 ]

Reference： [1]Patent: WO2011/119663,2011,A1

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[ 1337533-72-8 ]

Reference： [1]Patent: WO2011/119663,2011,A1

9
[ 1337533-31-9 ]
[ 1337532-29-2 ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 964 - 968

10
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[ 1337532-30-5 ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 964 - 968

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Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 964 - 968

12
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(4-fluoro-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine dihydrochloride [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 964 - 968

13
[ 1337533-31-9 ]
[ 73183-34-3 ]
[ 1037075-45-8 ]
[ 1337533-32-0 ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 964 - 968

14
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1,1-dimethylethyl 5-[5-amino-4-(aminocarbonyl)-1-methyl-1H-pyrazol-3-yl]4-fluoro-2,3-dihydro-1H-indole-1-carboxylate [ No CAS ]