[ CAS No. 893441-85-5 ] {[proInfo.proName]}

Name: 893441-85-5|6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one|95%
Brand: Ambeed
SKU: A154076
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Quality Control of [ 893441-85-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 893441-85-5 ]

SDS Specification

Alternatived Products of [ 893441-85-5 ]

Product Details of [ 893441-85-5 ]

CAS No. :	893441-85-5	MDL No. :	MFCD11855965
Formula :	C₁₄H₁₈BNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NXJYMGPXHVQNOT-UHFFFAOYSA-N
M.W :	259.11	Pubchem ID :	46739162
Synonyms :

Calculated chemistry of [ 893441-85-5 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	78.21
TPSA :	47.56 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.76
Log Po/w (WLOGP) :	0.91
Log Po/w (MLOGP) :	1.13
Log Po/w (SILICOS-IT) :	1.74
Consensus Log Po/w :	1.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.72
Solubility :	0.49 mg/ml ; 0.00189 mol/l
Class :	Soluble
Log S (Ali) :	-2.38
Solubility :	1.09 mg/ml ; 0.0042 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.49
Solubility :	0.00837 mg/ml ; 0.0000323 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.63

Safety of [ 893441-85-5 ]

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 [ 893441-85-5 ]

* 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 [ 893441-85-5 ]
Downstream synthetic route of [ 893441-85-5 ]

[ 893441-85-5 ] Synthesis Path-Upstream 1~4

1
[ 99365-40-9 ]
[ 73183-34-3 ]
[ 893441-85-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,2-dimethoxyethane at 80℃;	Four microwave vials were loaded as follows: 6-bromoindolin-2-one(500 mg, 2.36 mmol), bis(pinacolato)diboron (898 mg, 3.54 mmol),potassium acetate (694 mg, 7.07 mmol) and Pd(dppf)C12CH2C12 (96.0mg, 0.118 mmol) were dissolved in DME (17 mL). The reaction was heated at 80 °C overnight. The content of the four vials was then combined, concentrated and purified bycolumn chromatography (CyHex/EtOAc) to afford the title compound as a white solid (2.27 g, 75percent, purity 80percent). IH NMR (500 MHz, CDCI3) ppm = 8.57 (bs, IH), 7.48 (d, J7.3, IH), 7.31 (5, 1H), 7.23 (d, J=7.3, IH), 3.55 (s, 2H), 1.33 (s, 12H); LC — MS (ESI, mlz) Rt = 2.75 mm — 260 (M+H) (H PLC method E).
55%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In dimethyl sulfoxide at 90℃; for 18 h;	6-Brornoindohn-2-one 27) (2 00 u, 9 40 mmol) bispmacolatodiboron (6 00 g 23 60 mniol), potassium acetate (2.76g. 28.2 mmol) and diehloro[i,i’bis(dipheuylphosphino)feuocenrJj palladrum (11) dichloromethane addutt (0 40 g 0 55 rnniol) in DM80 (30 niL) were stirred at 90 °C tbr 18 hours, The reaction mixture was cooled to ambient temperature., then partitioned between water and ethyl acetate. Thelayers were separated and the aqueous layer extracted again with ethyl acetate (2x). The combined organic layers were washed with water and brine and concentrated to give a purple solid. The crude material was pre-absorbed onto Celite and chroniatographed (‘DCVC) eluting with a gradient of ethyl acetate in heptane (0 50percent ethyl. acetate.) Like fractions were combined and recrystallised from DCM and PE to give 6-(4,5,5-tetrainethyi—l,3,2—dioxahorolan—2yi)indoiin—2—one (24) as a colourless solid in 2 crops (1.33 g, 55percent); nip 178.5 181.4 °C. ‘H NMR (200 MHz, CDCI3) 8 8.61 (br s, 1H), 7.46 (d, 111. J7,4 Hz), 7.30 (s, lH), 7.21 (d. lH,J7.4 Hz), 3.53 (s, 2H). 1.32 (s. 1211).
40%	With potassium acetate In N,N-dimethyl-formamide at 95℃; for 18 h; Inert atmosphere; Sealed flask	6-bromoindolin-2-one (0.424 g; 2 mmol), potassium acetate (0.687 g; 7.0 mmol) and bis[pinacolato]diborane (0.762 g; 3.0 mmol) were placed in a 20 mL microwave vial, dissolved in dry DMF (13 mL) and the flask was purged with nitrogen. The catalyst [1 ,1 '- Bis(diphenylphosphino)ferrocene]palladium(ll) chloride, complex with dichloromethane (0.169 g; 0.20 mmol) was added, the flask was again purged with argon, sealed and the reaction was heated at 95⁰C for 18 h. The reaction mixture was diluted with water and the suspension was extracted twice with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (10 - 80 percent) in heptane furnished 0.390 g (40 percent) of the title compound.ESI/APCI(+): 260 (M₊H);1H NMR (DMSO-d6) δ 10.40 (s, 1 H), 7.27 (dd, J= 7,3, 0,8 Hz, 1 H), 7.21 (m, 1 H), 7.07 (s, 1 H), 3.50 (s, 2 H), 1.28 (s, 12 H).

39%	With potassium acetate In N,N-dimethyl-formamide at 90℃; for 16 h; Inert atmosphere	a) 6-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2- l)-1 ,3-dihydro-indol-2-one6-Bromo-1 ,3-dihydro-2H-indol-2-one (150 mg, 0.71 mmol), bis(pinacolato)diboron (233 mg, 0.92 mmol), KOAc (104 mg, 1.07 mmol) and Pd(dppf)CI₂ (29 mg) in anhydrous DMF (3 mL) were heated under N₂ at 90°C for 16 h. The mixture was diluted with EtOAc (40 mL) and washed with water (30 mL) then brine (30 mL). The organic layer was dried (Na₂S0₄) and concentrated in vacuo. Purification by column chromatography (MeOH-DCM gradient) gave a yellow solid (72 mg, 39percent); ¹H NMR (400 MHz, DMSO-d₆) δ 10.38 (s, 1 H), 7.27 (dd, J=7.3, 0.9 Hz, 1 H), 7.23 (d, J=7.3 Hz, 1 H), 7.07 (s, 1 H), 3.49 (s, 2H), 1.29 (s, 12H); m/z (ES+APCI)⁺: 260 [M+H]⁺.
22%	With potassium acetate In 1-methyl-pyrrolidin-2-one at 130℃; for 3 h;	To a solution of 6-bromo-2-oxindole (1 equiv) in NMP (0.05 M) were added bispinacolato diboron (2.4 equiv), potassium acetate (1.5 equiv), dppf (0.05 equiv) and PdCl₂(dppf) (0.05 equiv). The reaction mixture was stirred at 130°C for 3 hours and then concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The organic phase was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography on silica gel eluting with EtOAc/hexane (9 / 1), yielding the desired product as a red solid. 6-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-l,3-dihydro-indol-2-one: (22 percent yield, 51 percent purity main impurity being the boronic acid 28 percent) m/z (LC-MS, ESP): 260 [M+H]⁺ R/T = 3.51 min

Reference： [1] Patent: WO2015/144290, 2015, A1, . Location in patent: Page/Page column 85
[2] Patent: WO2015/39172, 2015, A1, . Location in patent: Page/Page column 60
[3] Patent: WO2011/15641, 2011, A1, . Location in patent: Page/Page column 128
[4] Patent: WO2011/101640, 2011, A1, . Location in patent: Page/Page column 106
[5] Patent: WO2008/23161, 2008, A1, . Location in patent: Page/Page column 120
[6] Patent: WO2006/66172, 2006, A1, . Location in patent: Page/Page column 77
[7] Patent: WO2014/63778, 2014, A1, . Location in patent: Page/Page column 46

2
[ 3460-18-2 ]
[ 893441-85-5 ]

Reference： [1] Patent: WO2015/39172, 2015, A1,

3
[ 1098855-11-8 ]
[ 893441-85-5 ]

Reference： [1] Patent: WO2015/39172, 2015, A1,

4
[ 100487-81-8 ]
[ 893441-85-5 ]

Reference： [1] Patent: WO2015/39172, 2015, A1,

[ 893441-85-5 ] Synthesis Path-Downstream 1~24

1
[ 1009303-44-9 ]
[ 893441-85-5 ]
[ 1217500-61-2 ]
C₂₅H₂₈N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; acetonitrile; at 110.0℃; for 0.166667h;Microwave radiation;	A mixture of the appropriate chloro-substrate (1 equiv), potassium carbonate (2.5 equiv), the appropriate pinacolate boron ester or boronic acid (1 equiv) and tetrakis(triphenylphosphine) palladium0 (0.05 equiv) was dissolved in acetonitrile/water (0.04 M of chloro-substrate). The reaction vessel was sealed and exposed to microwave radiation (110 0C, medium absorption setting) for 10 minutes. The crude residue was purified by column chromatography on silica gel eluting with 0 to 2 % MeOH in TBME to give the desired product.

Reference： [1]Patent: WO2008/23161,2008,A1 .Location in patent: Page/Page column 128; 179

2
[ 99365-40-9 ]
[ 73183-34-3 ]
[ 893441-85-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,2-dimethoxyethane; at 80℃;	Four microwave vials were loaded as follows: <strong>[99365-40-9]6-bromoindolin-2-one</strong>(500 mg, 2.36 mmol), bis(pinacolato)diboron (898 mg, 3.54 mmol),potassium acetate (694 mg, 7.07 mmol) and Pd(dppf)C12CH2C12 (96.0mg, 0.118 mmol) were dissolved in DME (17 mL). The reaction was heated at 80 C overnight. The content of the four vials was then combined, concentrated and purified bycolumn chromatography (CyHex/EtOAc) to afford the title compound as a white solid (2.27 g, 75%, purity 80%). IH NMR (500 MHz, CDCI3) ppm = 8.57 (bs, IH), 7.48 (d, J7.3, IH), 7.31 (5, 1H), 7.23 (d, J=7.3, IH), 3.55 (s, 2H), 1.33 (s, 12H); LC - MS (ESI, mlz) Rt = 2.75 mm - 260 (M+H) (H PLC method E).
55%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 90℃; for 18h;	6-Brornoindohn-2-one 27) (2 00 u, 9 40 mmol) bispmacolatodiboron (6 00 g 23 60 mniol), potassium acetate (2.76g. 28.2 mmol) and diehloro[i,i?bis(dipheuylphosphino)feuocenrJj palladrum (11) dichloromethane addutt (0 40 g 0 55 rnniol) in DM80 (30 niL) were stirred at 90 C tbr 18 hours, The reaction mixture was cooled to ambient temperature., then partitioned between water and ethyl acetate. Thelayers were separated and the aqueous layer extracted again with ethyl acetate (2x). The combined organic layers were washed with water and brine and concentrated to give a purple solid. The crude material was pre-absorbed onto Celite and chroniatographed (?DCVC) eluting with a gradient of ethyl acetate in heptane (0 50% ethyl. acetate.) Like fractions were combined and recrystallised from DCM and PE to give 6-(4,5,5-tetrainethyi-l,3,2-dioxahorolan-2yi)indoiin-2-one (24) as a colourless solid in 2 crops (1.33 g, 55%); nip 178.5 181.4 C. ?H NMR (200 MHz, CDCI3) 8 8.61 (br s, 1H), 7.46 (d, 111. J7,4 Hz), 7.30 (s, lH), 7.21 (d. lH,J7.4 Hz), 3.53 (s, 2H). 1.32 (s. 1211).
40%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 95℃; for 18h;Inert atmosphere; Sealed flask;	<strong>[99365-40-9]6-bromoindolin-2-one</strong> (0.424 g; 2 mmol), potassium acetate (0.687 g; 7.0 mmol) and bis[pinacolato]diborane (0.762 g; 3.0 mmol) were placed in a 20 mL microwave vial, dissolved in dry DMF (13 mL) and the flask was purged with nitrogen. The catalyst [1 ,1 '- Bis(diphenylphosphino)ferrocene]palladium(ll) chloride, complex with dichloromethane (0.169 g; 0.20 mmol) was added, the flask was again purged with argon, sealed and the reaction was heated at 950C for 18 h. The reaction mixture was diluted with water and the suspension was extracted twice with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (10 - 80 %) in heptane furnished 0.390 g (40 %) of the title compound.ESI/APCI(+): 260 (M+H);1H NMR (DMSO-d6) delta 10.40 (s, 1 H), 7.27 (dd, J= 7,3, 0,8 Hz, 1 H), 7.21 (m, 1 H), 7.07 (s, 1 H), 3.50 (s, 2 H), 1.28 (s, 12 H).

39%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 90℃; for 16h;Inert atmosphere;	a) 6-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2- l)-1 ,3-dihydro-indol-2-one6-Bromo-1 ,3-dihydro-2H-indol-2-one (150 mg, 0.71 mmol), bis(pinacolato)diboron (233 mg, 0.92 mmol), KOAc (104 mg, 1.07 mmol) and Pd(dppf)CI2 (29 mg) in anhydrous DMF (3 mL) were heated under N2 at 90C for 16 h. The mixture was diluted with EtOAc (40 mL) and washed with water (30 mL) then brine (30 mL). The organic layer was dried (Na2S04) and concentrated in vacuo. Purification by column chromatography (MeOH-DCM gradient) gave a yellow solid (72 mg, 39%); 1H NMR (400 MHz, DMSO-d6) delta 10.38 (s, 1 H), 7.27 (dd, J=7.3, 0.9 Hz, 1 H), 7.23 (d, J=7.3 Hz, 1 H), 7.07 (s, 1 H), 3.49 (s, 2H), 1.29 (s, 12H); m/z (ES+APCI)+: 260 [M+H]+.
22%	With potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1-methyl-pyrrolidin-2-one; at 130℃; for 3h;	To a solution of 6-bromo-2-oxindole (1 equiv) in NMP (0.05 M) were added bispinacolato diboron (2.4 equiv), potassium acetate (1.5 equiv), dppf (0.05 equiv) and PdCl2(dppf) (0.05 equiv). The reaction mixture was stirred at 130C for 3 hours and then concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The organic phase was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography on silica gel eluting with EtOAc/hexane (9 / 1), yielding the desired product as a red solid. 6-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-l,3-dihydro-indol-2-one: (22 % yield, 51 % purity main impurity being the boronic acid 28 %) m/z (LC-MS, ESP): 260 [M+H]+ R/T = 3.51 min
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 85℃; for 18h;	A solution of 0.17 g (0.82 mmol)of <strong>[99365-40-9]6-bromoindolin-2-one</strong>, 0.25 g of bis(pinacolato)diboron and 0.20 g (0.98 mmol) of KOAc in 5 mL of DMSO was degassed with Ar sparging for 5 min, then 33 mg (0.041 mmol) of 1,1'- bis(diphenylphosphino)ferrocene-palladium(II) dichloride was added and the reaction solution was stirred at 85 0C for 18 h. The reaction solution was poured into 250 mL ofEtOAc, washed twice with a 1 M aqueous solution Of MgSO4, once with brine, then concentrated in vacuo, and purified by flash chromatography eluting with a linear gradient of 20% EtOAc in hexane to neat EtOAc to yield the title compound. MS (M+H)+ 260.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,2-dimethoxyethane; at 80℃;	Four microwave vials were loaded as follows: 6-Bromoindolin-2-one (500 mg, 2.36 mmol), bis(pinacolato)diboron (898 mg, 3.54 mmol), potassium acetate (694 mg, 7.07 mmol) and Pd(dppf)Cl2*CH2Cl2 (96.0 mg, 0.118 mmol) were dissolved in DME (17 mL). The reaction was heated at 80 C overnight. The content of the four vials was then combined, concentrated and purified by column chromatography (cyclohexane/EtOAc) to afford the title compound as a white solid (2.27 g, 75%, purity 80%). 1 H NMR (500 MHz, CDCl3) ppm = 8.57 (bs, 1 H), 7.48 (d, J=7.3, 1 H), 7.31 (s, 1 H), 7.23 (d, J=7.3, 1 H), 3.55 (s, 2H), 1.33 (s, 12H). LC - MS (ESI, m/z) Rt = 2.75 min - 260 (M+H)+ (HPLC method B).

Reference： [1]Patent: WO2015/144290,2015,A1 .Location in patent: Page/Page column 85
[2]Patent: WO2015/39172,2015,A1 .Location in patent: Page/Page column 60
[3]Patent: WO2011/15641,2011,A1 .Location in patent: Page/Page column 128
[4]Patent: WO2011/101640,2011,A1 .Location in patent: Page/Page column 106
[5]Patent: WO2008/23161,2008,A1 .Location in patent: Page/Page column 120
[6]Patent: WO2006/66172,2006,A1 .Location in patent: Page/Page column 77
[7]Patent: WO2014/63778,2014,A1 .Location in patent: Page/Page column 46

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 1.5h;Inert atmosphere;	General procedure: To R8 (100 mg, 0.47 mmol) in anhydrous dioxane (8 mL) is added R5 (180 mg, 0.71 mmol) and potassium acetate (140mg, 1.43 mmol). The mixture is purged with Argon, PdCl2(dppf) (40 mg, 0.049 mmol) added and heated to 80 C for 1.5 h. The reaction mixture is diluted with EA and water, the organic layer washed with brine, dried and concentrated. The crude product is carried on. m/z 260 [M+H]+, rt 0.64 min LC-MS Method b.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 1.5h;Inert atmosphere;	General procedure: To R8 (100 mg, 0.47 mmol) in anhydrous dioxane (8 mL) is added R5 (180 mg, 0.71 mmol) and potassium acetate (140 mg, 1.43 mmol). The mixture is purged with Argon, PdCl2(dppf) (40 mg, 0.049 mmol) added and heated to 80 C. for 1.5 h. The reaction mixture is diluted with EA and water, the organic layer washed with brine, dried and concentrated. The crude product is carried on. m/z 260 [M+H]+, rt 0.64 min, LC-MS Method b.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃; for 2h;Inert atmosphere;	General procedure: Step 3: Synthesis of Intermediate R7 To 1-12.2 (32.0 g, 142 mmol) in anhydrous dioxane (400 mL) is added R3 (54.4 g, 241 mmol) and potassium acetate (41.6 g, 424 mmol). The mixture is purged with Argon, [1, - Bis(diphenylphosphino)ferrocene]dichloropalladium(II) as a complex with dichloromethane (11.2 g, 14 mmol) is added and the mixture is heated to 90 C for 2 h. The reaction mixture is diluted with ethyl acetate and water, the organic layer is washed with water, dried over MgS04 and concentrated. The residue is purified via flash chromatography (cyclohexane / EA = 70:30). Yield 72%, m/z 274 [M+H]+, rt 0.67 min, LC-MS Method V011_S01.

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃; for 2h;

General procedure: To I-12.2 (32.0 g, 142 mmol) in anhydrous dioxane (400 mL) is added R3 (54.4 g, 241 mmol) and potassium acetate (41.6 g, 424 mmol). The mixture is purged with Argon, [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) as a complex with dichloromethane (11.2 g, 14 mmol) is added and the mixture is heated to 90 C. for 2 h. The reaction mixture is diluted with ethyl acetate and water, the organic layer is washed with water, dried over MgSO4 and concentrated. The residue is purified via flash chromatography (cyclohexane/EA=70:30). Yield 72%, m/z 274 [M+H]+, rt 0.67 min, LC-MS Method V011_S01.

4
[ 893441-85-5 ]
[ 1196551-90-2 ]
[ 1196546-34-5 ]

Yield	Reaction Conditions	Operation in experiment
	With water; sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 150℃; for 20h;Inert atmosphere;	In step 2-6, a suspension of 4-(3-bromoimidazo[l,2-b]pyridazin-6-yl)-3-(3- fluorophenyl)morpholine (25 mg, 0.067 mmol), 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)indolin-2- one (34 mg, 0.13 mmol) and [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (2.7 mg, 0.0033 mmol) in 3 mL of 1, 4-dioxane and 0.5 mL of 2.0M sodium carbonate was bubbled with nitrogen and heated to 150 0C and stirred for 20 hours. The solution was cooled to room temperature and purified with HPLC to afford 6-(6-(3-(3-fluorophenyl)mophiholino)imidazo[l,2-b]pyridazin-3-yl)indolin-2-one (2-6) as a white solid.

Reference： [1]Patent: WO2009/140128,2009,A2 .Location in patent: Page/Page column 103

5
[ 893441-85-5 ]
[ 1333509-01-5 ]
[ 1333507-24-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 150℃; for 1h;Inert atmosphere; microwave irradiation;	A mixture of l-(2-(6-chloroimidazo[l ,2-a]pyridin-8-ylamino)-6,7- dihydropyrazolo[l ,5-fl]pyrazin-5(4H)-yl)ethanone (89 mg, 0.27 mmol) and 6-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)indolin-2-one (90 mg, 0.35 mmol) in 1 M aqueous sodium carbonate (0.54 mL) and 1,4-dioxane (2 mL) was sparged with nitrogen while stirring for 5 min. Tetrakis(triphenylphosphine)palladium(0) (62 mg, 0.054 mmol) was then added and the reaction heated under microwave irradiation at 150 C for 1 h. After this time, the mixture was filtered through diatomaceous earth and the filter cake washed with a mixture of 3:7 methanol/methylene chloride (100 mL). The filtrate was washed with water (20 mL), then brine (20 mL) and diied over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography (silica, gradient, methylene chloride to 19: 1 methylene chloride/methanol) to afford 6-(8-(5-acetyl-4,5,6,7-tetrahydropyrazolo[l,5-a]pyrazin-2- ylamino)imidazo[l ,2-a]pyridm-6-yl)indolin-2-one as an orange-brown solid: mp 161-165 C; 'H NMR (400 MHz, D SO-cfe, 107 Cd 10.09 (bs, 1H), 8.15-8.14 (m, 2H), 7.86 (d, J = 1.2 Hz, 1H), 7.78 (d, J= 1.6 Hz, 1H), 7.47 (d, J = 1.2 Hz, 1H), 7.27 (d, J = 7.6 Hz, 1H), 7.17 (dd, J= 7.6, 1.6 Hz, 1H), 7.05 (d, J = 1.2 Hz, 1H), 6.04 (s, 1H), 4.68 (s, 2H), 4.06 (t, J= 5.6 Hz, 2H), 3.93 (t, J= 5.6 Hz, 2H), 3.47 (s, 2H), 2.10 (s, 3H); ESI MS m/z 428.2 [M + H]+; HPLC, 4.06 min, >99% (AUC).
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 150℃; for 1h;Inert atmosphere; Microwave irradiation;	Preparation of 6-(8-(5-acetyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)imidazo[1,2-a]pyridin-6-yl)indolin-2-one A mixture of 1-(2-(6-chloroimidazo[1,2-a]pyridin-8-ylamino)-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)ethanone (89 mg, 0.27 mmol) and <strong>[893441-85-5]6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one</strong> (90 mg, 0.35 mmol) in 1 M aqueous sodium carbonate (0.54 mL) and 1,4-dioxane (2 mL) was sparged with nitrogen while stirring for 5 min. Tetrakis(triphenylphosphine)palladium(0) (62 mg, 0.054 mmol) was then added and the reaction heated under microwave irradiation at 150 C. for 1 h. After this time, the mixture was filtered through diatomaceous earth and the filter cake washed with a mixture of 3:7 methanol/methylene chloride (100 mL). The filtrate was washed with water (20 mL), then brine (20 mL) and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography (silica, gradient, methylene chloride to 19:1 methylene chloride/methanol) to afford 6-(8-(5-acetyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)imidazo[1,2-a]pyridin-6-yl)indolin-2-one as an orange-brown solid: mp 161-165 C.; 1H NMR (400 MHz, DMSO-d6, 107 d 10.09 (bs, 1H), 8.15-8.14 (m, 2H), 7.86 (d, J=1.2 Hz, 1H), 7.78 (d, J=1.6 Hz, 1H), 7.47 (d, J=1.2 Hz, 1H), 7.27 (d, J=7.6 Hz, 1H), 7.17 (dd, J=7.6, 1.6 Hz, 1H), 7.05 (d, J=1.2 Hz, 1H), 6.04 (s, 1H), 4.68 (s, 2H), 4.06 (t, J=5.6 Hz, 2H), 3.93 (t, J=5.6 Hz, 2H), 3.47 (s, 2H), 2.10 (s, 3H); ESI MS m/z 428.2 [M H]+; HPLC, 4.06 min, >99% (AUC).

Reference： [1]Patent: WO2011/112995,2011,A1 .Location in patent: Page/Page column 44; 46
[2]Patent: US2014/148430,2014,A1 .Location in patent: Paragraph 0319

6
[ 893441-85-5 ]
[ 1333509-16-2 ]
[ 1333507-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 150℃; for 1h;Inert atmosphere; microwave irradiation;	A mixture of 2-(3-(6-chloroimidazo[l ,2-fl]pyi-idin-8-ylamiiio)-l -methyl-lH-pyrazol- 5-yl)propan-2-ol (250 mg, 0.818 mmol), 6-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2- yl)indolin-2-one (275 mg, 1.06 mmol) and 1 M aqueous sodium carbonate (2.5 mL) in 1 ,4- dioxane (3 mL) was sparged with nitrogen while stirring for 5 min.Tetrakis(triphenylphosphine)palladium(0) (94 mg, 0.081 mmol) was then added and the reaction heated under microwave irradiation at 150 C for 60 min. After this time, the reaction was cooled to room temperature, diluted with a mixture of 1 :9 methanol/methylene chloride (150 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, methylene chloride to 1 :4 methanol/methylene chloride), then trituration with acetonitrile, followed by trituration with methanol to afford 6-(8-(5-(2-hydroxypropan-2-yl)-l-methyl-lH- pyrazol-3-ylamino)imidazo[ 1 ,2-a]pyridin-6-yl)indolin-2-one as a light yellow solid: mp 180-182 C; NMR (400 MHz, DMSO- )d 10.54 (s, 1H), 8.61 (s, 1H), 8.25 (d, J = 1.6 Hz, lH), 8.04 (d, J= 1.2 Hz, 1H), 7.91 (d, J= 1.2 Hz, 1H), 7.51 (d, J = 0.8 Hz, 1H), 7.31 (d, J= 7.6 Hz, 1 H), 7.21 (dd, J = 7.6, 1.6 Hz, 1H), 7.06 (d, J= 0.8 Hz, 1 H), 5.99 (s, 1H), 5.27 (s, 1H), 3.92 (s, 3H), 3.53 (s, 2H), 1.50 (s, 6H); ESI MS m/z 403.1 [M + H]+; HPLC, 4.30 min, >99% (AUC).
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 150℃; for 1h;Inert atmosphere; Microwave irradiation;	Preparation of 6-(8-(5-(2-hydroxypropan-2-yl)-1-methyl-1H-pyrazol-3-ylamino)imidazo[1,2-a]pyridin-6-yl)indolin-2-one A mixture of 2-(3-(6-chloroimidazo[1,2-a]pyridin-8-ylamino)-1-methyl-1H-pyrazol-5-yl)propan-2-ol (250 mg, 0.818 mmol), <strong>[893441-85-5]6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one</strong> (275 mg, 1.06 mmol) and 1 M aqueous sodium carbonate (2.5 mL) in 1,4-dioxane (3 m L) was sparged with nitrogen while stirring for 5 min. Tetrakis(triphenylphosphine)palladium(0) (94 mg, 0.081 mmol) was then added and the reaction heated under microwave irradiation at 150 C. for 60 min. After this time, the reaction was cooled to room temperature, diluted with a mixture of 1:9 methanol/methylene chloride (150 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, methylene chloride to 1:4 methanol/methylene chloride), then trituration with acetonitrile, followed by trituration with methanol to afford 6-(8-(5-(2-hydroxypropan-2-yl)-1-methyl-1H-pyrazol-3-ylamino)imidazo[1,2-a]pyridin-6-yl)indolin-2-one as a light yellow solid: mp 180-182 C.; 1H NMR (400 MHz, DMSO-d6.) 10.54 (s, 1H), 8.61 (s, 1H), 8.25 (d, J=1.6 Hz, 1H), 8.04 (d, J=-1.2 Hz, 1H), 7.91 (d, J=1.2 Hz, 1H), 7.51 (d, J=0.8 Hz, 1H), 7.31 (d, J=7.6 Hz, 1H), 7.21 (dd, J=7.6, 1.6 Hz, 1H), 7.06 (d, J=0.8 Hz, 1H), 5.99 (s, 1H), 5.27 (s, 1H), 3.92 (s, 3H), 3.53 (s, 2H), 1.50 (s, 6H); ESI MS m/z 403.1 [M+H]+; HPLC, 4.30 min, >99% (AUC).

Reference： [1]Patent: WO2011/112995,2011,A1 .Location in patent: Page/Page column 58-60
[2]Patent: US2014/148430,2014,A1 .Location in patent: Paragraph 0350

7
[ 893441-85-5 ]
[ 1333509-21-9 ]
[ 1333507-31-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 145℃; for 0.5h;Inert atmosphere; microwave irradiation;	A mixture of 2-(6-(6-chloroimidazo[ l ,2-a]pyridin-8-ylamino)pyridiii-3-yl)-2- methylpropan-l -ol (195 mg, 0.616 mmol), 6-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2- yl)indolin-2-one (176 mg, 0.679 mmol) and 1 M aqueous sodium carbonate (0.5 mL) in 1 ,4- dioxane (2 mL) was sparged with nitrogen while stirring for 5 min.[0296] Tetrakis(triphenylphosphine)palladium(0) (107 mg, 0.0925 mmol) was then added and the reaction heated under microwave irradiation at 145 C for 30 min. After this time, the reaction was cooled to room temperature, diluted with a mixture of 1 :4methanol/methylene chloride (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified bychromatography (silica, gradient, methylene chloride to 1 : 19 methanol/methylene chloride), then trituration with methanol to afford 6-(8-(5-(l -hydroxy-2-methylpropan-2-yl)pyridin-2- ylamino)imidazo[l,2-a]pyridin-6-yl)indolin-2-one as a light pink-orange solid: mp 260-266 C dec; NMR (400 MHz, DMSO-<¾)d 10.50 (s, 1H), 9.02 (s, 1H), 8.65 (d, J= 1.2 Hz, 1H), 8.37 (d, J = 1.2 Hz, 1 H), 8.26 (d, J= 2.4 Hz, 1H), 7.96 (d, J = 0.8 Hz, 1H), 7.67 (dd, J = 8.8, 2.8 Hz, 1H), 7.55 (d, J= 0.8 Hz, 1H), 7.36^7.32 (m, 2H), 7.23 (dd, J- 7.6, 1.6 Hz, 1H), 7.07 (d, J = 0.8 Hz, 1H), 4.70 (t, J= 7.2 Hz, 1 H), 3.54 (s, 2H), 3.41 (d, J = 7.2 Hz, 2H), 1.24 (s, 6H); ESI MS m/z 414.4 [M + H]+; HPLC, 4.07 min, >99% (AUC).
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 145℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Preparation of 6-(8-(5-(1-hydroxy-2-methylpropan-2-yl)pyridin-2-ylamino)imidazo[1,2-a]pyridin-6-yl)indolin-2-one A mixture of 2-(6-(6-chloroimidazo[1,2-a]pyridin-8-ylamino)pyridin-3-yl)-2-methylpropan-1-ol (195 mg, 0.616 mmol), <strong>[893441-85-5]6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one</strong> (176 mg, 0.679 mmol) and 1 M aqueous sodium carbonate (0.5 mL) in 1,4-dioxane (2 mL) was sparged with nitrogen while stirring for 5 min. Tetrakis(triphenylphosphine)palladium(0) (107 mg, 0.0925 mmol) was then added and the reaction heated under microwave irradiation at 145 C. for 30 min. After this time, the reaction was cooled to room temperature, diluted with a mixture of 1:4 methanol/methylene chloride (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, methylene chloride to 1:19 methanol/methylene chloride), then trituration with methanol to afford 6-(8-(5-(1-hydroxy-2-methylpropan-2-yl)pyridin-2-ylamino)imidazo[1,2-a]pyridin-6-yl)indolin-2-one as a light pink-orange solid: mp 260-266 C. dec; 1H NMR (400 MHz, DMSO-d6.) 10.50 (s, 1H), 9.02 (s, 1H), 8.65 (d, J=1.2 Hz, 1H), 8.37 (d, J=1.2 Hz, 1H), 8.26 (d, J=2.4 Hz, 1H), 7.96 (d, J=0.8 Hz, 1H), 7.67 (dd, J=8.8, 2.8 Hz, 1H), 7.55 (d, J=0.8 Hz, 1H), 7.36-7.32 (m, 2H), 7.23 (dd, J=7.6, 1.6 Hz, 1H), 7.07 (d, J=0.8 Hz, 1H), 4.70 (t, J=7.2 Hz, 1H), 3.54 (s, 2H), 3.41 (d, J=7.2 Hz, 2H), 1.24 (s, 6H); ESI MS m/z 414.4 [M+H]+; HPLC, 4.07 min, >99% (AUC).

Reference： [1]Patent: WO2011/112995,2011,A1 .Location in patent: Page/Page column 60; 63; 64
[2]Patent: US2014/148430,2014,A1 .Location in patent: Paragraph 0358-0359

8
[ 893441-85-5 ]
[ 1352151-91-7 ]
[ 1352152-04-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In water; acetonitrile; at 80℃; for 2h;Inert atmosphere;	(i) (S)-tert-Buty l-(l-amino-l-oxo-3-(4-(2-oxoindolin-6-yl)phenyl)propan-2- ylcarbamoyl)cyclohexylcarbamatePotassium carbonate (161 mg) was added in water (1.6 mL) to (S)-tert-butyl l-(l-amino-3-(4- iodophenyl)-l-oxopropan-2-ylcarbamoyl)cyclohexylcarbamate (Example 6, step (i), 300 mg), 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)indolin-2-one (151 mg) and 1,1 bis(di-tert- butylphosphino)ferrocene palladium dichloride (49.3 mg) in degassed acetonitrile (5 mL) at 20C under an atmosphere of nitrogen. The resulting solution was stirred at 80C for 2 h. The reaction mixture was allowed to cool to room temperature, filtered, evaporated then partitioned between ethyl acetate and water. The organics were dried over magnesium sulfate and evaporated to afford crude material as a brown gum. The crude product was absorbed onto Celite and purified by chromatography on silica eluting with 70% to 100% ethyl acetate in z'sohexane. Pure fractions were evaporated to dryness to afford the sub-titled compound (221 mg). 1H NMR (500 MHz, DMSO) delta 10.43 (s, 1H), 7.50 (d, 1H), 7.46 (d, 2H), 7.25 (t, 4H), 7.20 (s, 1H), 7.16 (dd, 1H), 6.98 (s, 1H), 6.95 (s, 1H), 4.48 - 4.40 (m,lH), 3.50 (s, 2H), 3.15 (d, 1H), 2.93 (dd, 1H), 1.74 - 1.64 (m, 3H), 1.48 - 1.38 (m, 3H), 1.35 (s, 10H), 1.32 - 1.22 (m, 2H), 1.15 - 1.08 (m, 1H). m/e (APCI+) 521 [M+H]+

Reference： [1]Patent: WO2011/154677,2011,A1 .Location in patent: Page/Page column 63-64

9
[ 893441-85-5 ]
aq. Na₂CO₃ [ No CAS ]
[ 1417190-42-1 ]
[ 1417183-94-8 ]

Yield	Reaction Conditions	Operation in experiment
	Pd(PPh3)4; In 1,4-dioxane;	Example 241 6-[2-(2-Imidazo[1,2-a]pyridin-2-yl-ethyl)-3-oxo-2,3-dihydro-1H-isoindol-4-yl]-1,3-dihydro-indol-2-one A 5 mL microwave reaction vial was charged with 7-bromo-2-(2-imidazo[1,2-a]pyridin-2-yl-ethyl)-2,3-dihydro-isoindol-1-one from Example 20.1 (100 mg, 0.281 mmol), <strong>[893441-85-5]6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one</strong> (87 mg, 0.337 mmol) and aq. Na2CO3 (2 N, 0.5 mL) in dioxane (2 mL). Pd(PPh3)4 (3.24 mg, 2.81 mumol) was added. The resulting suspension was heated on microwave at 100 C. for 30 minutes. The solid was filtered. The filtrated was purified by Prep-HPLC to give the title compound (24.5 mg, 0.060 mmol, 21.37% yield). LC-MS: m/z=409 (M+H+); Rt=1.74 min. 1H NMR (400 MHz, DMSO-d6): delta=10.40 (s, 1H), 8.46 (d, J=6.4 Hz, 1H), 7.62-7.45 (m, 3H), 7.33-7.31 (m, 1H), 7.23-7.16 (m, 2H), 7.01-7.00 (m, 1H), 6.94 (s, 1H), 6.84-6.80 (m, 1H), 4.47 (s, 2H), 3.86 (t, J=6.8 Hz, 2H), 3.52 (s, 2H). 3.03 (t, J=7.2 Hz, 2H).

Reference： [1]Patent: US2013/5705,2013,A1

10
[ 893441-85-5 ]
[ 1607837-99-9 ]
[ 1607837-13-7 ]

Yield	Reaction Conditions	Operation in experiment
35%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; acetonitrile; at 120℃; for 1h;Microwave irradiation; Inert atmosphere;	8-(2-Amino-5-bromo-3-chloropyridin-4-yl)-2,8-diazaspiro[4.5]decan-1-one (15.0 mg, 0.042 mmol), <strong>[893441-85-5]6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one</strong> (11.9 mg, 0.046 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.41 mg, 2.09 pmol) were loaded in a microwave vial. The capped vial was evacuated using high vacuum and purged with nitrogen (each three times). Acetonitrile (0.4 mL) and aqueous sodium carbonate (0.5M, 0.18 mL, 0.058 mmol) were added and the mixture was degassed using high vacuum and purged with nitrogen again three times. The mixture was heated in the microwave at 120 C for 1 h before it was transferred into a flask with the help of chloroform/methanol and the water was evaporated by azeotropic removal with toluene twice. The resulting residue was purified by chromatography on silica gel (dichloromethane/ethanol) and recrystallization from ethyl acetate/diethyl ether to give the title compound as a white solid (6.0 mg, 35%). 1H-NMR (500 MHz, DMSO-d6) ppm = 10.39 (s, 1 H), 7.61 (s, 1 H), 7.52 (s, 1 H), 7.23 (d, J=7.6, 1 H), 6.81 (dd, J=7.5, 1 .3 , 1 H), 6.68 (s, 1 H), 6.11 (s, 2H), 3.51 (s, 2H), 3.12 (t, J=6.8 , 2H), 2.95 (d, J=12.6, 2H), 2.65 (d, J=9.8, 2H), 1.82 (t, J=6.8, 2H), 1.71 (td, J=12.6, 3.6, 2H), 1.23 (d, J=12.6, 2H). HRMS m/z (ESI+) [M+H]+ C2iH23CI 502, calc 412.1535, found 412.1526, Rt = 1 .72 min (HPLC method B).

Reference： [1]Patent: WO2014/63778,2014,A1 .Location in patent: Page/Page column 25; 76

11
[ 893441-85-5 ]
[ 1533423-93-6 ]
6-[4'-(5-amino-1H-[1,2,4]triazol-3-ylamino)-2',6'-dichlorophenyl]-1,3-dihydroindol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In water; butan-1-ol; at 135℃; for 0.5h;Inert atmosphere; Microwave irradiation;	To a 1 5 m L microwave vial was added N3-(4-bromo-3,5-dichlorophenyl)-lH-l ,2,4-triazole-3,5- diamine Intermediate 2 (201 mg, 622 iimol, Eq: 1 .00), 6-(4,4,5,5-tetramethyl-l ,3,2- dio.xaborolan-2-yl )indolii]-2-one (161 mg, 622 iimol, Eq: 1 .00) and CS2CO3(507 mg, 1 .56 mmol, Eq: 2.5) in n-BuOH (3.00 ml ) and Water (600 mu). PdCl2(DPPF) (40.7 mg, 49.8 iimol, Eq : 0.08) was added, the mixture was purged with argon, the vial was capped and heated in the microwave at 135C for 30 min. Diluted with diehloromethane, added a S0 and filtered through cel ite. The filtrate was concentrated and the crude material was purified by preparative I I PLC(0.1%TFA in water/0.1 % TFA in AcCN) 95% to 10% TFA water over 25m ins. Dried under vacuum overnight to afford 29 mg (12%) of the desired product as a light yellow sol id.MS -m/z: 372.9/374.9 (m- 1 )

Reference： [1]Patent: WO2014/135495,2014,A1 .Location in patent: Page/Page column 417

12
[ 893441-85-5 ]
C₂₂H₂₈BrN₃O₃ [ No CAS ]
C₃₀H₃₄N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In water; acetonitrile; at 80℃; for 14h;Inert atmosphere;	R6 (34 mg, 0.13 mmol) and I-2.2 (46 mg, 0.10 mmol) are put together in vented acetonitrile (3 mL) and then aq. potassium carbonate solution (2 mol/L, 1000-) is added. Then 1,1-Bis(di-tert-butylphosphino)ferrocene palladium dichloride (7 mg, 0.01 mmol) is added quickly and the reaction vessel is purged with argon. The reaction mixture is heated to 80 C. for 2 h. Further 0.5 eq of educt R6 and further 0.1 eq of the catalyst are added and the reaction mixture is stirred at 80 C. for additional 12 h. The resulting mixture is filtrated over a mixture of basic aluminium oxide and silica gel 1/1. The residue is purified by reversed phase HPLC. Yield 41% m/z 514 [M+H]+, rt 0.92 min, LC-MS Method Z018_S04.
41%	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate; In water; acetonitrile; at 80℃; for 14h;Inert atmosphere;	Step 3: Synthesis of Intermediate 1-2.3R6 (34 mg, 0.13 mmol) and 1-2.2 (46 mg, 0.10 mmol) are put together in vented acetonitrile (3 mE) and then aq. potassium carbonate solution (2 mol/L, 100 jiL) is added. Then 1,1-Bis(di-tert- butylphosphino)ferrocene palladium dichloride (7 mg, 0.01 mmol) is added quickly and thereaction vessel is purged with argon. The reaction mixture is heated to 80 C for 2 h. Further 0.5eqof educt R6 and further 0.1 eq of the catalyst are added and the reaction mixture is stirred at 80Cfor additional 12 h. The resulting mixture is filtrated over a mixture of basic aluminium oxide andsilica gel 1/1. The residue is purified by reversed phase HPLC. Yield 41% m/z 514 [M+H]+, it 0.92mm, LC-MS Method Z018 504.

Reference： [1]Patent: US2014/275159,2014,A1 .Location in patent: Paragraph 0294; 0297
[2]Patent: WO2014/140091,2014,A1 .Location in patent: Page/Page column 62

13
[ 3460-18-2 ]
[ 893441-85-5 ]

Reference： [1]Patent: WO2015/39172,2015,A1

14
[ 1098855-11-8 ]
[ 893441-85-5 ]

Reference： [1]Patent: WO2015/39172,2015,A1

15
[ 893441-85-5 ]
3-formylbiphenyl-4-yl trifluoromethanesulfonate [ No CAS ]
4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-[1 1‘-biphenyl]-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; ethanol; water; at 110℃; for 2h;Sealed tube;	To a suspension of 2-oxo-2,3 -dihydro- 1 H-benzo imidazo le-5 -boronic acid pinaco 1 ester (24) (574 mg, 2.2 mmol), 3-formylbiphenyl-4-yl trifluoromethanesulfonate (14) (663 mg,2.0 mmol) and sodium carbonate (426 mg, 4.0 mmol) in degassed dioxane/ethanollH2O(5:1:1, 20 mL) was added tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.1 mmol).The reaction was heated at 110 C for 2 h in a sealed tube. Analysis by TLC (1:2DCM;PE) indicated the triflate had been consumed. The reaction was concentrated todryness, then taken up in equal volumes of DCM and water and stirred vigorously for 20minutes, ensuring all lumps were broken up and a fine precipitate was achieved. Thesolid was collected by filtration through hardened ashless paper (540) on a Buchner funnel, and washed thoroughly with DCM and water. The solid was dried in vacuo at 40 C to affhrd 4-(2-oxo-2.3-dihydro-i Fi-benzo[d]imidazol-5-yi)-[i .1 -hiphenyi]-3-carbaldehyde (28) (365 mg, 58%) as a pale yellow solid. ?H NMR (200 MHz, DMSO-d4)6 10.82 (brs, 2H), 9.95 (s, 1H), 8.15 7.96 m, 214), 7.76 (rn, 214), 7.68 7.36 (in, 411),7.12 6.95 (m, 3H). ?CNMR(50 MHz, DMSO-d) 6 192.1, 155.4, 144.6, 139.1, 138.7,133.7, 131.8, 131.7. 130.1, 130.0. 129.2, 128.0, 126.7, 125.1. 122.9, 109,7, 108.4 (one signal not observed). ElMS: ink Found: W? 314.1 050, C20H,4O2N2requires 314.1055. ElMS: ink 314 (M. 100%)..

Reference： [1]Patent: WO2015/39172,2015,A1 .Location in patent: Page/Page column 62; 63

16
[ 893441-85-5 ]
(E)-3-(3-amino-3-oxoprop-1-en-1-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate [ No CAS ]
(E)-3-(4-(2-oxoindolin-6-yl)-[1,1'-biphenyl]-3-yl)acrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene;	Prepared according to the method used to generate PS; from (E)-3-(3-aniino-3-oxoprop-I-cn-l-yl)-[l,i ?-biphenyl]-4-yl trifluorometlianesulfOnatc (23) (0.50 g, 1.35 mmnol), 6-4 4 5 5-tetiamethvl-l,3 2-dioxahorolan-2yl)mdohn-2-one (241 (0 43 g 1 68 mmol tetiakisttnphcn lphosphme)palladium(0) (0 100 g 0 09 innwl) and aqueous sodium carbonate (JM) (3,0 mL, 3.00 nmmol) in toluene (10 mE) and ethanol (2 niL). The crude material was collected by filtration from the aqueous work-up, then purified by triturationin DCM and methnnol 1.0 give (T)-3-(4-(2-oxindolm-6-yl)-[ 11 -bip&nylj-3- 1)aciylamidc (25) as pale lemon needles (0 36 g 75%) mp 263 - 26?C (Dec )NMR (400 MHz DMSO-d6) 6 10 47 (s 1H), 7 95 (s lH), 7 80 7 70 (in, 3H) 7 57737(m 5H),7460,rs 1111 732d 111, 17611/) 7 l2hts 1H),6X9d III 176Hz). 6.80 -6.72 (m, 2H), 3.55 (s, 2H). 13C NMR (100 MHz, DMSO-d6) 6 177.4, 166.5,143.9, 141.1, 139.6, 139,4, 138.8, 137.4, 133.1, 130.9, 129.0. 127.8, 127.6, 126.8, 125.3,124.4, 124.3, 123.7, 122.6, 110.1,35.6. ElMS: ith Found: ivr 354.1356, C23H18N202 requires 354.1363. ElMS: tn/z 354 (M?, 13%), 310 (100). 309 (43).

Reference： [1]Patent: WO2015/39172,2015,A1 .Location in patent: Page/Page column 61

17
[ 893441-85-5 ]
(E)-3-(3-amino-3-oxoprop-1-en-1-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate [ No CAS ]
3-(4-(2-oxoindolin-6-yl)-[1,1‘-biphenyl]-3-yl)propanamide [ No CAS ]

Reference： [1]Patent: WO2015/39172,2015,A1

18
[ 893441-85-5 ]
(E/Z)-3-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-[1,1'-biphenyl]-3-yl)acrylamide [ No CAS ]

Reference： [1]Patent: WO2015/39172,2015,A1

19
[ 893441-85-5 ]
3-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-[1,1'-biphenyl]-3-yl)propanamide [ No CAS ]

Reference： [1]Patent: WO2015/39172,2015,A1

20
[ 100487-81-8 ]
[ 893441-85-5 ]

Reference： [1]Patent: WO2015/39172,2015,A1

21
[ 893441-85-5 ]
[ 1257307-01-9 ]
6-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)indolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 120℃; for 2h;	To a mixture of 6-fluoro-3-iodo-1 -(phenylsulfonyl)-1 /-/-indole (Intermediate 1 , 600 mg, 1 .50 mmol), 6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)indolin-2-one (259 mg, 1 .00 mmol, prepared as described in WO2014140075) and K2CO3 (276 mg, 2.00 mmol) in dioxane (10 imL) and water (1 imL) was added Pd(PPh3)4 (1 16 mg, 0.10 mmol). The mixture was stirred at 120 C for 2 hrs before it was concentrated. The residue was purified by silica gel chromatography (petroleum ether/EtOAc = 5/1 , v/v) to afford 400 mg (98%) of the title compound as a yellow solid. 1 H NMR (300 MHz, CDCI3) delta [ppm]: 7.96 - 7.90 (m, 2H), 7.81 (dd, J = 9.6, 2.4 Hz, 1 H), 7.70 - 7.63 (m, 3H), 7.61 - 7.56 (m, 1 H), 7.54 - 7.45 (m, 2H), 7.31 (d, J = 7.7 Hz, 1 H), 7.22 (dd, J = 7.7, 1 .5 Hz, 1 H), 7.10 - 7.01 (m, 2H), 3.59 (s, 2H).

Reference： [1]Patent: WO2015/140717,2015,A1 .Location in patent: Page/Page column 148; 149

22
[ 893441-85-5 ]
[ 1257307-01-9 ]
6-(6-fluoro-1H-indol-3-yl)indolin-2-one [ No CAS ]

Reference： [1]Patent: WO2015/140717,2015,A1

23
[ 893441-85-5 ]
(2-bromoethyl)(diphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]
6'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		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

24
[ 893441-85-5 ]
[ 106-45-6 ]
6-(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-3-(p-tolylthio)indolin-2-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 14342 - 14348

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Precautionary Statements-General
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Code	Phrase
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P270	Do not eat, drink or smoke when using this product.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
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Response
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P321
P322
P330	Rinse mouth.
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P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
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P372	Explosion risk in case of fire.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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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
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H221	Flammable gas
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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
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Health hazards
Code	Phrase
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H310	Fatal in contact with skin
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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
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H332	Harmful if inhaled
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H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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H340	May cause genetic defects
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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

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[ 893441-85-5 ] Synthesis Path-Upstream 1~4

[ 893441-85-5 ] Synthesis Path-Downstream 1~24

Related Functional Groups of [ 893441-85-5 ]

Organoboron

Amides

Related Parent Nucleus of [ 893441-85-5 ]

Indolines

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[ 893441-85-5 ]

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[ 893441-85-5 ]