[ CAS No. 1150271-44-5 ]

Name: 1150271-44-5|4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one|95%
Brand: Ambeed
SKU: A181793
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Quality Control of [ 1150271-44-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1150271-44-5 ]

SDS Specification

Alternatived Products of [ 1150271-44-5 ]

Product Details of [ 1150271-44-5 ]

CAS No. :	1150271-44-5	MDL No. :	MFCD11504971
Formula :	C₁₄H₁₈BNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LDDMKYKRLRAKPL-UHFFFAOYSA-N
M.W :	259.11 g/mol	Pubchem ID :	46739223
Synonyms :

Calculated chemistry of [ 1150271-44-5 ]

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 :	2.85

Safety of [ 1150271-44-5 ]

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 [ 1150271-44-5 ]

* 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 [ 1150271-44-5 ]
Downstream synthetic route of [ 1150271-44-5 ]

[ 1150271-44-5 ] Synthesis Path-Upstream 1~1

1
[ 99365-48-7 ]
[ 73183-34-3 ]
[ 1150271-44-5 ]

Yield	Reaction Conditions	Operation in experiment
74%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 110℃; for 2 h; Sealed tube; Microwave irradiation	Intermediate 114: 4-(4,4,5,5-Tetramethyl-1 ,2-dioxaborolan-2-yl)indolin-2-one (0793) A mixture of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (1.903 g, 7.49 mmol, commercially available from, for example, Fluorochem), 4-bromoindolin-2-one (1.038 g, 4.90 mmol, commercially available from, for example, Fluorochem), [1,1'- 7 s(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane [Pd(dppf)Cl2.DCM] (0.601 g, 0.73 mmol) and potassium acetate (1.480 g, 15.08 mmol) in 1,4-dioxane (30 mL) was stirred at 110 °C for 2 h. The mixture was allowed to cool to rt before being filtered through a 10 g celite cartridge. The cartridge was washed through with ethyl acetate (3 x 30 mL) and the combined filtrates were evaporated in vacuoto give a brown liquid which was re-dissolved in DCM (ca. 10 mL), loaded onto a 100 g SNAP silica cartridge and purified by Biotage SP4 semi-automated flash column chromatography eluting with a gradient of 20 to 50percent ethyl acetate in cyclohexane. The required fractions were combined and evaporated in vacuo, this was re-dissolved in DCM (ca. 10 mL), transferred to a tarred vial and the solvent evaporated under a stream of nitrogen. The residue was triturated with ether (5 x 5 mL), decanting away the mother liquor each time, and the residue dried under a stream of nitrogen and in vacuo to give the desired product 4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)indolin-2-one (941.8 mg, 3.63 mmol, 74 percent yield) as a cream solid. (0794) LCMS (2 min Formic): Rt = 0.93 min, [MH]+ = 260.3.
74.2%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 110℃; for 2 h;	A mixture of 4,4,4T,4T,5,5,5T,5T-octamethyl-2,2T-bi( 1,3, 2-d ioxaborolane) (1.9025 g, 7.49 mmol), 4-bromoindolin-2-one (1.0383 g, 4.90 mmol), [1,1’-Bis(d iphenylphosphino)ferrocene]dichloropallad ium(II), complex with dichloromethane (0.6005 g,0.734 mmol) and potassium acetate (1.4802 g, 15.08 mmol) in 1,4-Dioxane (30 mL) was stirred at110 °C for 2 hr. The mixture was allowed to cool to room temperature before being filtered througha lOg celite cartridge. The cartridge was washed through with ethyl acetate (3 x 30 mL) and thecombined filtrates were evaporated in vacuo to give to give a brown liquid, which was redissolved indichloromethane (ca. 10 mL), loaded onto a bOg SNAP silica cartridge and purified by Biotage 5P4semi-automated flash column chromatography eluting with a gradient of 20 to 50percent ethyl acetate incyclohexane. The required fractions were combined and evaporated in vacuo, the residue (which was on the verge of crystallisation) was re-dissolved in dichloromethane (ca. 10 mL), transferred to a tared vial, the solvent evaporated under a stream of nitrogen. The residue was triturated with ether (5 x 5 mL), decanting away the mother liquor each time, and the residue dried under a stream of nitrogen and in vacuoto give the desired product as a cream solid (941.8 mg, 3.63 mmol, 74.2 percent yield)LCMS (2 mm Formic): Rt = 0.93 mi [MH]+ = 260

Reference： [1] Patent: WO2017/174621, 2017, A1, . Location in patent: Page/Page column 88
[2] Patent: WO2017/202742, 2017, A1, . Location in patent: Page/Page column 42; 43; 97; 98

[ 1150271-44-5 ] Synthesis Path-Downstream 1~16

2
[ 1150271-44-5 ]
[ 1000342-95-9 ]
[ 76-05-1 ]
4-(6-(trifluoromethyl)-1H-indazol-4-yl)indolin-2-one trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%		EXAMPLE 129: 4-(6-(trifluoromethyl)-lH-indazol-4-yl)indolin-2-one [0548] A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-lH-indazole (0.026 g, 0.096 mmol), 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)indolin-2-one (0.025 g, 0.096 mmol) and PdCl2(dppf) (3.53 mg, 4.82 muiotaetaomicron) in dioxane (4 mL) and aqueous saturated NaHC03 (3 mL). The resulting light brown suspension was heated at 140°C for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with 30percent ACN (containing 0.035percent) TFA) in H20 (containing 0.05percent TFA) over a period of 10 minutes. The product-containing fractions were combined and volatiles evaporated in vacuo to give a TFA salt of the title compound as a light brown solid (0.014 g, 0.044 mmol, 46percent). 1H NMR (400 MHz, DMSO- d6) delta ppm 3.50 (s, 2 H), 6.94 (d, J=7.58 Hz, 1 H), 7.17 (dd, J=7.96, 0.88 Hz, 1 H), 7.29-7.44 (m, 1 H), 7.46-7.53 (m, 1 H), 7.94 (s, 1 H), 8.15 (s, 1 H), 10.55 (s, 1 H), 13.70 (s, 1 H); ESI- MS m/z [M+H]+ calc'd for C16H10F3N3O, 318.1; found 318.15.

Reference： [1]Patent: WO2013/130855,2013,A1 .Location in patent: Paragraph 0547; 0548

3
[ 1150271-44-5 ]
4-[4-chloro-6-(morpholin-4-yl)-8-oxa-3,5,1 0triazatricyclo[7.4.0.02,7]trideca1(13),2(7),3,5,9,11-hexaen-12-yl]methyl}-1λ4-thiomorpholin-1-one [ No CAS ]
4-[6-(morpholin-4-yI)-12-[(1-oxo-1λ4-thiomorpholin-4-yI)methyl]-8-oxa-3,5,10-triazatricycIo[7.4.0.02,7]trideca-1(13),2(7),3,5,9,11-hexaen-4-yI]-2,3-dihydro-1H-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 2h;Inert atmosphere; Microwave irradiation;	To a microwave vial containing Intermediate 8 (117 mg, 0.278 mmol, 1.0 eq), <strong>[1150271-44-5](2-oxoindolin-4-yl)boronic acid pinacol ester</strong> (152 mg, 0.556 mmol, 2.0 eq), sodium carbonate (58.9 mg, 0.556 mmol, 2.0 eq) and PdCl2(PPh3)2 (39.0 mg, 0.0556 mmol, 20 mol%) was added 1,4-dioxane (1.1 mL) and H20 (0.3 mL). Thesuspension was stirred at 90C for 1 h in a microwave reactor then cooled to rt. An additional portion of PdCI2(PPh3)2 (19.5 mg, 0.0278 mmol, 10 mol%) was added and the reaction mixture was heated at 90C for a further 1 h in the microwave. Upon cooling, the mixture was diluted with CH2CI2 (20 mL) and washed with H20 (20 mL). The aqueous layer was concentrated in vacuo andpurified by silica gel column chromatography with CH2CI2/MeOH (1:0-9:1). The product was re-dissolved in CH2CI2/MeOH (4:1, 15 mL) and swirled with prewashed MP-TMT resin (200 mg, 0.220 mmol, 3 eq wrt Pd) at rtfor 17 h. The solution was filtered and the resin washed with CH2CI2/MeOH (4:1, 100 mL) to yield Example N as an off-white solid (79.7 mg, 55%).1H NMR (300MHz, DMSO-d5) oH. 10.49 (5, 1H), 8.62 (br 5, 2H), 8.02 (d, J=8.1Hz, 1H), 7.34 (t, J=7.8 Hz, 1H), 6.95 (d, J=7.5 Hz, 1H), 4.04-4.18 (m, 4H), 3.99(5, 2H), 3.73-3.93 (m, 6H), 2.85-3.06 (m, 4H), 2.66-2.84 (m, 4H).MS (ESj 519.2 (100%, [M+H]j, 541.2 (12%, [M+Na]j.

Reference： [1]Patent: WO2017/29521,2017,A1 .Location in patent: Page/Page column 80

4
[ 1150271-44-5 ]
cis-3-(2-chloropyrimidin-5-yl)-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one [ No CAS ]
cis-8-dimethylamino-3-[2-(2-oxo-1,3-dihydroindol-4-yl)-pyrimidin-5-yl]-8-phenyl-1,3-diazaspiro[4.5]decan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With bis(tri-t-butylphosphine)palladium(0); sodium carbonate; In tetrahydrofuran; water; at 23 - 60℃;	CIS-3-(2-chloropyrimidin-5-yl)-8-(dimethylamino)-8-phenyl-l,3-diazaspiro[4.5]decan-2-one (INT- 989) (150 mg, 0.38 mmol), Pd(t-Bu3P)2 (0.1 equiv., 0.02 mmol, 10 mg) and 4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)indolin-2-one (2 equiv., 0.78 mmol, 201 mg) were dissolved in degassed anhydrous THF (80 equiv., 31 mmol, 2.5 mL) and 1M aq. Na2CO3 (5.5 equiv., 2.14 mmol, 2.14 mL) was added. The resulting mixture was stirred at 60C for 8 h and then at RT overnight. The reaction mixture was diluted with water until precipitation occurred. The precipitate was filtered off, suspended in 30 mL DCM, filtered off again, washed with pentane (5 mL) and dried under reduced pressure to give 143 mg (76%) of CIS-4-(5-(8-(dimethylamino)-2- oxo-8-phenyl-l ,3-diazaspiro[4.5]decan-3-yl)pyrimidin-2-yl)indolin-2-one (SC_3208). :H NMR (600 MHz, DMSO) delta 10.45 (s, IH), 9.10 (s, 2H), 7.87 (d, IH), 7.84 - 7.80 (m, IH), 7.39 (d, 5H), 7.29 (dt, 2H), 6.91 (d, IH), 3.82 (s, 2H), 3.72 (s, 2H), 2.41 (d, 2H), 2.03 - 1.74 (m, 9H), 1.60 - 1.44 (m, 3H). Mass: m/z 484.26 (M+H)+.

Reference： [1]Patent: WO2017/121647,2017,A1 .Location in patent: Paragraph 0390; 0391

5
[ 99365-48-7 ]
[ 73183-34-3 ]
[ 1150271-44-5 ]

Yield	Reaction Conditions	Operation in experiment
74%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 110℃; for 2h;Sealed tube; Microwave irradiation;	Intermediate 114: 4-(4,4,5,5-Tetramethyl-1 ,2-dioxaborolan-2-yl)indolin-2-one (0793) A mixture of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (1.903 g, 7.49 mmol, commercially available from, for example, Fluorochem), <strong>[99365-48-7]4-bromoindolin-2-one</strong> (1.038 g, 4.90 mmol, commercially available from, for example, Fluorochem), [1,1'- 7 s(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane [Pd(dppf)Cl2.DCM] (0.601 g, 0.73 mmol) and potassium acetate (1.480 g, 15.08 mmol) in 1,4-dioxane (30 mL) was stirred at 110 C for 2 h. The mixture was allowed to cool to rt before being filtered through a 10 g celite cartridge. The cartridge was washed through with ethyl acetate (3 x 30 mL) and the combined filtrates were evaporated in vacuoto give a brown liquid which was re-dissolved in DCM (ca. 10 mL), loaded onto a 100 g SNAP silica cartridge and purified by Biotage SP4 semi-automated flash column chromatography eluting with a gradient of 20 to 50% ethyl acetate in cyclohexane. The required fractions were combined and evaporated in vacuo, this was re-dissolved in DCM (ca. 10 mL), transferred to a tarred vial and the solvent evaporated under a stream of nitrogen. The residue was triturated with ether (5 x 5 mL), decanting away the mother liquor each time, and the residue dried under a stream of nitrogen and in vacuo to give the desired product 4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)indolin-2-one (941.8 mg, 3.63 mmol, 74 % yield) as a cream solid. (0794) LCMS (2 min Formic): Rt = 0.93 min, [MH]+ = 260.3.
74.2%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 110℃; for 2h;	A mixture of 4,4,4T,4T,5,5,5T,5T-octamethyl-2,2T-bi( 1,3, 2-d ioxaborolane) (1.9025 g, 7.49 mmol), <strong>[99365-48-7]4-bromoindolin-2-one</strong> (1.0383 g, 4.90 mmol), [1,1?-Bis(d iphenylphosphino)ferrocene]dichloropallad ium(II), complex with dichloromethane (0.6005 g,0.734 mmol) and potassium acetate (1.4802 g, 15.08 mmol) in 1,4-Dioxane (30 mL) was stirred at110 C for 2 hr. The mixture was allowed to cool to room temperature before being filtered througha lOg celite cartridge. The cartridge was washed through with ethyl acetate (3 x 30 mL) and thecombined filtrates were evaporated in vacuo to give to give a brown liquid, which was redissolved indichloromethane (ca. 10 mL), loaded onto a bOg SNAP silica cartridge and purified by Biotage 5P4semi-automated flash column chromatography eluting with a gradient of 20 to 50% ethyl acetate incyclohexane. The required fractions were combined and evaporated in vacuo, the residue (which was on the verge of crystallisation) was re-dissolved in dichloromethane (ca. 10 mL), transferred to a tared vial, the solvent evaporated under a stream of nitrogen. The residue was triturated with ether (5 x 5 mL), decanting away the mother liquor each time, and the residue dried under a stream of nitrogen and in vacuoto give the desired product as a cream solid (941.8 mg, 3.63 mmol, 74.2 % yield)LCMS (2 mm Formic): Rt = 0.93 mi [MH]+ = 260
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 12h;Inert atmosphere;	A mixture of <strong>[99365-48-7]4-bromoindolin-2-one</strong> (500.0 mg, 2.36 mmol), B2pin2 (898.2mg, 3.54 mmol), KOAc (462.8 mg, 4.72 mmol), Pd(dppt)Ch (172.5 mg, 235.80 umol) indioxane (20 mL) was degassed and purged with N2 for 3 times, and then the mixture wasstirred at 80 oc for 12h under N2 atmosphere. The mixture was concentrated and theresulting residue was purit1ed by column chromatography (Si02, Petroleum ether/Ethylacetate= 10/1 to 0:1). Compound 115A (600.0 mg, crude) was obtained as a yellow solid.Tiw crude product was used in next step directly.

Reference： [1]Patent: WO2017/174621,2017,A1 .Location in patent: Page/Page column 88
[2]Patent: WO2017/202742,2017,A1 .Location in patent: Page/Page column 42; 43; 97; 98
[3]Patent: WO2019/190885,2019,A1 .Location in patent: Paragraph 0469

6
[ 1150271-44-5 ]
(±)-tert-butyl 2-(methylcarbamoyl)-6-(1-(2-oxoindolin-4-yl)ethyl)isonicotinate [ No CAS ]

Reference： [1]Patent: WO2017/174621,2017,A1
[2]Patent: WO2017/202742,2017,A1

7
[ 1150271-44-5 ]
(±)-2-(methylcarbamoyl)-6-(1-(2-oxoindolin-4-yl)ethyl)isonicotinic acid [ No CAS ]

Reference： [1]Patent: WO2017/174621,2017,A1
[2]Patent: WO2017/202742,2017,A1

8
[ 1150271-44-5 ]
(±)-N4-((1R,5S,6r)-3-oxabicyclo[3.1.0]hexan-6-yl)-N2-methyl-6-(1-(2-oxoindolin-4-yl)ethyl)pyridine-2,4-dicarboxamide [ No CAS ]

Reference： [1]Patent: WO2017/174621,2017,A1

9
[ 1150271-44-5 ]
(±)-N4-((1R,5S,6r)-3-oxabicyclo[3.1.0]hexan-6-yl)-N2-methyl-6-((R)-1-(2-oxoindolin-4-yl)ethyl)pyridine-2,4-dicarboxamide [ No CAS ]
(±)-N4-((1R,5S,6r)-3-oxabicyclo[3.1.0]hexan-6-yl)-N2-methyl-6-((S)-1-(2-oxoindolin-4-yl)ethyl)pyridine-2,4-dicarboxamide [ No CAS ]

Reference： [1]Patent: WO2017/174621,2017,A1

10
[ 1150271-44-5 ]
tert-butyl 2-(1-bromovinyl)-6-(methylcarbamoyl)isonicotinate [ No CAS ]
tert-butyl 2-(methylcarbamoyl)-6-(1-(2-oxoindolin-4-yl)vinyl)isonicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium phosphate; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In 1,4-dioxane; water; at 20℃; for 19h;Inert atmosphere; Darkness;	Intermediate 176: te -Butyl 2-(methylcarbamov0-6-(l-(2-oxoindolin-4- vOvinvOisonicotinate (1022) (1023) A solution of fe/f-butyl 2-(l-bromovinyl)-6-(methylcarbamoyl)isonicotinate (350 mg, 0.72 mmol), 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)indolin-2-one (276.9 mg, 1.07 mmol), [1,3- 7/5(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride (PEPPSI-iPr) (71.0 mg, 0.10 mmol) and tripotassium phosphate (566.8 mg, 2.67 mmol) in 1,4-dioxane (6 mL) and water (3 mL) was stirred under nitrogen at rt in the dark for 19 h. The reaction mixture was filtered through a 2.5 g celite cartridge and the cartridge washed with ethyl acetate (approx. 10 mL). To the filtrate was added water (5 mL) and brine (5 mL) and the layers separated. The aqueous layer was extracted with further ethyl acetate (2 x 10 mL) and the organic phases were combined and filtered through a cartridge fitted with a hydrophobic frit. The filtrate was evaporated in vacuoto give a sticky brown solid (556.7 mg). This was redissolved in DMSO (6 mL) and directly purified by MDAP (high pH). The required fractions were combined and evaporated in vacuo to give fe/f-butyl 2- (methylcarbamoyl)-6-(l-(2-oxoindolin-4-yl)vinyl)isonicotinate (157.7 mg, 0.40 mmol, 56 % yield) as a light yellow solid. (1024) LCMS (2 min High pH): Rt = 1.05 min, [MH]+ = 394.4
36.2%	With potassium phosphate; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In 1,4-dioxane; water; at 20℃; for 22.5h;Inert atmosphere; Darkness;	A solution of tert-butyl 2-(1-bromovinyl)-6-(methylcarbamoyl)isonicotinate (380 mg, 0.724 mmol), <strong>[1150271-44-5]4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one</strong> (250.3 mg, 0.966 mmol), [1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)pallad ium(II) d ichloride (51.9 mg, 0.076 mmol) and tripotassium phosphate (492.6 mg, 2.321 mmol) in 1,4-Dioxane (4.0 mL) and Water (2.0 mL) was stirred at room temperature under nitrogen in the dark for 22.5 hours. To the reaction mixture was added ethyl acetate (15 mL), water (10 mL) and brine (5 mL) and the layers separated. Theaqueous layer was extracted with further ethyl acetate (2 x 15 mL) and the organic phases were combined and filtered through a cartridge fitted with a hydrophobic frit. The filtrate was evaporated in vacuo to give a sticky light brown solid (415.0 mg). This was redissolved in DMSO (4 mL) and methanol (2 mL) and directly purified by (MDAP) (2 x 3 mL injection, high pH). The required fractions were combined and evaporated in vacuo to give the desired product as a yellow solid (103.2 mg,0.262 mmol, 36.2 % yield).LCMS (2 mm High pH): Rt = 1.05 mi [MH]+ = 394

Reference： [1]Patent: WO2017/174621,2017,A1 .Location in patent: Page/Page column 120
[2]Patent: WO2017/202742,2017,A1 .Location in patent: Page/Page column 98

11
[ 1150271-44-5 ]
2-(methylcarbamoyl)-6-((2-oxoindolin-4-yl)methyl)isonicotinic acid [ No CAS ]

Reference： [1]Patent: WO2017/202742,2017,A1

12
[ 1150271-44-5 ]
N₂-methyl-N₄-((1S,2S)-2-methylcyclopropyl)-6-(1-(2-oxoindolin-4-yl)ethyl)pyridine-2,4-dicarboxamide [ No CAS ]

Reference： [1]Patent: WO2017/202742,2017,A1

13
[ 1150271-44-5 ]
N₂-methyl-N₄-((1S,2S)-2-methylcyclopropyl)-6-((2-oxoindolin-4-yl)methyl)pyridine-2,4-dicarboxamide [ No CAS ]

Reference： [1]Patent: WO2017/202742,2017,A1

14
[ 1150271-44-5 ]
tert-butyl 2-(chloromethyl)-6-(methylcarbamoyl)isonicotinate [ No CAS ]
tert-butyl 2-(methylcarbamoyl)-6-((2-oxoindolin-4-yl)methyl)isonicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33.3%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 120℃; for 0.666667h;	tert-Butyl 2-(chloromethyl)-6-(methylcarbamoyl)isonicotinate (80 mg, 0.281 mmol) was combined with 4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)indolin-2-one (479 mg, 0.425 mmol, 23% wt.),potassium carbonate (129.9 mg, 0.940 mmol) and PdCI2(dppf) (41.1 mg, 0.056 mmol) in 1,4-dioxane (1 mL) and water (0.5 mL) in a 2 mL microwave vial. This was heated at 120 C for 40 mm. The solution was filtered through Celite (eluent EtOAc) then concentrated to give 198 mg of a black solid. This was purified by chromatography on Si02 (Biotage SNAP 10 g, eluting with lO-S0% ethyl acetate/cyclohexane). The desired fractions were concentrated to give tert-butyl 2-(methylcarbamoyl)-6-((2-oxoindolin-4-yl)methyl)isonicotinate (39.7 mg, 0.094 mmol, 33.3 % yield) as a colourless oil.LCMS (2 mm Formic): Rt = 1.00 mi [MH]+ 382.3.

Reference： [1]Patent: WO2017/202742,2017,A1 .Location in patent: Page/Page column 55; 56

15
[ 1048982-04-2 ]
[ 1150271-44-5 ]
C₁₃H₁₁N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis(tri-t-butylphosphine)palladium(0); caesium carbonate; In 1,4-dioxane; water; at 80℃; for 1h;Inert atmosphere;	A mixture of ethyl 4-chloro-1,2,5-thiadiazole-3-carboxylate (446.0 mg,2.32 mmol), compound H5A (600.0 mg, 2.32 mmol), palladium;tritert-butylphosphane(118.3 mg, 231.56 umol), Cs2C03 (2.26 g, 6.95 mmo1) in rhO (5 mL) and dioxane (50 mL)was degassed and purged with N2 for 3 times, and then the mixture was stirred at 80 oc for lhr under N2 atmosphere. The mixture was concentrated and the resulting residue waspurified by column chromatography (Si02, Petroleum ether/Ethyl acetate=5/l to 0: l ).Compound 115B (500.0 mg, 50.3% yield, 67.4% purity) was obtained as a yellow solid. MS(ESI) m/z (M+Ht 290.0.

Reference： [1]Patent: WO2019/190885,2019,A1 .Location in patent: Paragraph 0469; 0470

16
[ 1150271-44-5 ]
C₁₁H₇N₃O₃S [ No CAS ]

Reference： [1]Patent: WO2019/190885,2019,A1

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[ CAS No. 1150271-44-5 ]

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[ 1150271-44-5 ] Synthesis Path-Upstream 1~1

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Organoboron

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