[ CAS No. 1256359-21-3 ] {[proInfo.proName]}

Name: 1256359-21-3|Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carboxylate|96%
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SKU: A368555
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2D 3D

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Quality Control of [ 1256359-21-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1256359-21-3 ]

SDS Specification

Alternatived Products of [ 1256359-21-3 ]

Product Details of [ 1256359-21-3 ]

CAS No. :	1256359-21-3	MDL No. :	MFCD11858368
Formula :	C₁₆H₂₀BNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MOQAIXOQKOUHGG-UHFFFAOYSA-N
M.W :	301.15	Pubchem ID :	53217131
Synonyms :

Calculated chemistry of [ 1256359-21-3 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.44
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	86.05
TPSA :	60.55 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) :	-6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.92
Log Po/w (WLOGP) :	2.25
Log Po/w (MLOGP) :	1.31
Log Po/w (SILICOS-IT) :	2.36
Consensus Log Po/w :	1.77

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.65
Solubility :	0.0672 mg/ml ; 0.000223 mol/l
Class :	Soluble
Log S (Ali) :	-3.85
Solubility :	0.0423 mg/ml ; 0.00014 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.95
Solubility :	0.00339 mg/ml ; 0.0000113 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.11

Safety of [ 1256359-21-3 ]

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 [ 1256359-21-3 ]

* 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.

Downstream synthetic route of [ 1256359-21-3 ]

[ 1256359-21-3 ] Synthesis Path-Downstream 1~5

1
[ 1422006-32-3 ]
[ 1256359-21-3 ]
[ 2140148-57-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane for 2h; Inert atmosphere; Reflux;	General Method 4 - representative procedure (0904) Methyl 2-(4-amino- 1-isopropyl- 1H-pyrazolo[3, 4-d]pyrimidin-3-yl)- 1 H-indole-6-carboxylate (Intermediate 27) (0905) [00215] A mixture of 3-bromo-1-isopropyl-1 /-/-pyrazolo[3,4-d]pyrimidin-4-amine (0.4 g, 1.56 mmol) and methyl 2-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 /-/-indole-6- carboxylate (0.47 g, 1.56 mmol) in 1 ,4-dioxane (10 mL) was degassed with nitrogen. Pd(dppf)CI2 DCM (32 mg, 0.04 mmol) was added followed by 1.8 M K2C03 (1.74 mL, 3.12 mmol). The reaction mixture was heated at reflux for 2 hours then cooled to room temperature, diluted with EtOAc (50 mL) and washed with water (2 χ 25 mL). The combined aqueous phases were back-extracted with EtOAc (50 mL). The combined organics were washed with brine (50 mL) then concentrated in vacuo and purified by fee (0-100% EtOAc in isohexane) to return the title compound (438 mg, 80%) as a yellow solid. LCMS [M+H]+ 351.2; 1 H NMR (300 MHz, DMSO-de) δ 1 1.98 (br s, 1 H), 8.28 (s, 1 H), 8.15 (s, 1 H), 7.65-7.74 (m, 2H), 7.16 (br s, 1 H), 6.96 (s, 1 H), 5.12 (quin, J = 6.64 Hz, 1 H), 3.88 (s, 3H), 1.55 (d, J = 6.78 Hz, 6H).

Reference： [1]Current Patent Assignee: CANCER RESEARCH UK - WO2017/178844, 2017, A1 Location in patent: Paragraph 00215

2
[ 1422006-32-3 ]
[ 1256359-21-3 ]
[ 2140148-59-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 2 h / Inert atmosphere; Reflux 2: N-chloro-succinimide / N,N-dimethyl-formamide / 1 h / 20 °C

Reference： [1]Current Patent Assignee: CANCER RESEARCH UK - WO2017/178844, 2017, A1

3
[ 1256359-21-3 ]
[ 2413300-89-5 ]
[ 2413301-86-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 1.5h; Inert atmosphere;	86.1 Step 1: Preparation of methyl 2-(6-(3-((tert-butyldimethylsilyl)oxy)propyl)-4-((2,4- dimethoxybenzylamino-7-isopropyl-7H-pyrrolo[2.3-dlpyrimidin-5-yl-lH-indole-6-carboxylate. A mixture of 6-(3-((tert-butyldimethylsilyl)oxy)propyl)-N-(2,4-dimethoxybenzyl)-5-iodo-7-isopropyl-7H- pyrrolo[2,3-d]pyrimidin-4-amine (Intermediate P33) (1.0 g, 1.6 mmol), 6-methoxycarbonyl-lH-indole-2- boronic acid pinacol ester (1.45 g, 4.8 mmol) , PdCUiPPhs (0.22 g, 0.32 mmol), and Na2C03 (2 N, aq) (2154) (1.6 mL, 3.2 mmol) in dioxane (23 mL) was sparged with argon and heated to 80 °C for 90 min. After cooled to rt, the reaction was diluted with water and extracted with DCM (3x). The combined organic extracts were concentrated and purified by silica chromatography (0-100% EtOAc in hexanes) to afford the title compound (958 mg, 89%). MS (apci) m/z = 672.4 (M+H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2020/55672, 2020, A1 Location in patent: Page/Page column 339

4
[ 1256359-21-3 ]
[ 2365356-87-0 ]
[ 2413300-68-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere;	Intermediate P26 (1770) (1771) Methyl 2-(6-(((tert-butyldimethylsilyl)oxy)methyl)-4-((2,4-dimethoxybenzyl)amino)-7-isopropyl-7H- pyrrolo[2,3-d1pyrimidin-5-yl)-lH-indole-6-carboxylate A mixture of 6-methoxycarbonyl-lH-indole-2-boronic acid pinacol ester (852 mg, 2.83 mmol), (1773) (PPhs)2Pd(ll)Cl2 (99.3 mg, 0.141 mmol), 6-(((tert-butyldimethylsilyl)oxy)methyl)-N-(2,4- dimethoxybenzyl)-5-iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (Intermediate P14) (422 mg, 0.707 mmol) and Na2C03 (2 N aq) (707 m, 1.41 mmol) in dioxane (10 mL) was sparged with Ar and heated at 80 °C for 2 h. The reaction was partitioned between DCM and water then extracted with 4:1 DCM:IPA (3x). The combined organic extracts were concentrated and purified using silica (1774) chromatography (0-40% EtOAc in hexanes) to yield the title product (415 mg, 91%). MS (apci) m/z = 644.3 (M+H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2020/55672, 2020, A1 Location in patent: Page/Page column 281-282

5
[ 1256359-21-3 ]
[ 2413300-56-6 ]
[ 2413300-72-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃;	1 Step 1: Preparation of methyl 2-(6-(3-(benzyloxy)-3-oxopropyl)-4-((2.4-dimethoxybenzyl)amino)-7- isopropyl-7H-pyrrolo[2.3-dlpyrimidin-5-yl)-lH-indole-6-carboxylate. A mixture of methyl 2-(4, 4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole-6-carboxylate (0.318 g, 1.05 mmol), benzyl 3-(4-((2,4- dimethoxybenzyl)amino)-5-iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)propanoate (Intermediate P16) (0.108 g, 0.176 mmol), PdCI2(PPh3)2 (0.0123 g, 0.0176 mmol) and Na2C03 (2 N, aq) (0.27 ml, 0.54 mmol) in dioxane (0.88 mL) was heated to 90 °C overnight. The reaction mixture was then filtered, concentrated and purified by silica chromatography (1-15% MeOH in DCM) to give the title compound (0.116 g, 99%). MS (apci) m/z = 662.3 (M+H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2020/55672, 2020, A1 Location in patent: Page/Page column 283-284

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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
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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. 1256359-21-3 ] {[proInfo.proName]}

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Physicochemical Properties

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Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 1256359-21-3 ]

[ 1256359-21-3 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 1256359-21-3 ]

Organoboron

Esters

Related Parent Nucleus of [ 1256359-21-3 ]

Indoles

Precautionary Statements-General

Prevention

Response

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Health hazards

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Related Functional Groups of
[ 1256359-21-3 ]

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[ 1256359-21-3 ]