[ CAS No. 1313441-88-1 ]

Name: 1313441-88-1|tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)carbamate|98%
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SKU: A501330
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Quality Control of [ 1313441-88-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1313441-88-1 ]

CAS No. :	1313441-88-1	MDL No. :	MFCD21602848
Formula :	C₂₀H₃₀BNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	359.27 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 1313441-88-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1313441-88-1 ]

* 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 [ 1313441-88-1 ]

[ 1313441-88-1 ] Synthesis Path-Downstream 1~20

1
[ 24424-99-5 ]
[ 1313441-88-1 ]

Reference： [1]Patent: US2016/96834,2016,A1
[2]Patent: WO2016/102672,2016,A2
[3]Patent: US2012/108574,2012,A1

2
[ 360773-84-8 ]
[ 73183-34-3 ]
[ 1313441-88-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 70℃; for 12h;Inert atmosphere;	A mixture of <strong>[360773-84-8]tert-butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate</strong> (3 g, 9.61 mmol, CAS360773-84-8), Pin2B2 (4.88 g, 19.2 mmol), KOAc (2.83 g, 28.8 mmol) and cyclopentyl(diphenyl) phosphane; dichloromethane; dichloropalladium; iron (392 mg, 480 umol) in DMSO (30 mL) was degassed and then heated to 70 C. for 12 hours under N2. On completion, the mixture was quenched with water (200 mL) and filtered. The filter cake was purified by silica gel chromatography (SiO2) to give the title compound (3.0 g, 87% yield) as a white solid. LC-MS (ESI+) m/z 398.2 (M+K)+.
80%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃; for 5h;	Step 2: Preparation of tert-butyl {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl}carbamate A suspension of tert-butyl[1(4-bromophenyl)cyclopropyl]carbamate (400 mg) and 4,4,4',4',5,5,5',51-octamethyl-2,2'-bi-1,3,2-dioxaborolane (390 mg) and potassium acetate (377 mg) and PdCl2(dppf)CH2Cl2 (31 mg) in dimethylsulfoxide (6.5 mL) was degassed for 5 min then stirred at 80 C. for 5 h. The reaction mixture was diluted with benzene and filtered. The filtrate was washed with brine (5 times). The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (0-20% ethyl acetate in hexanes) gave the product (367 mg, 80%). 1HNMR (CDCl3) 400 MHz delta: 7.73 (d, J=8.3 Hz, 2H), 7.19 (d, J=8.3 Hz, 2H), 5.25 (br s, 1H), 1.47-1.18 (m, 25H).
	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In N,N-dimethyl-formamide; at 100℃;	5-tert-butyl-N-(1-[4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]cyclopropyl)-1,2,4-oxadiazole-3-carboxamide 22.6 mg (2.1% for 6 steps) was prepared from <strong>[360773-84-8]tert-butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate</strong>, 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane, 4-chloro-3-nitropyridin-2-amine and 5-tert-butyl-1,2,4-oxadiazole-3-carboxylate using Method 19R, 2J, 1G, 15P, 19T and 11N. HPLC: 99.9% purity. MS: m/z=483.1 [M+H]+. 1H NMR (400 MHz, CD3OD): delta 8.45-8.25 (m, 2H), 8.23-8.15 (m, 1H), 8.05-8.01 (m, 1H), 7.75 (s, 1H), 7.53-7.52 (m, 2H), 7.35-7.25 (m, 1H), 4.01 (s, 3H), 1.52 (s, 9H), 1.48 (s, 4H).

1.46 g	With potassium acetate; palladium diacetate; XPhos; In acetonitrile; at 80℃;Inert atmosphere;	Step 2: tert-butyl (l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)cyclopropyl)carbamate: The product from Step 1 above (1.43 g, 4.50 mmol, 98% purity), b 5,-(pinacolato)diboron (1.39 g, 5.48 mmol), palladium(II) acetate (0.051 g, 0.229 mmol), X-Phos (0.219 g, 0.457 mmol) and potassium acetate (1.35 g, 13.7 mmol) were combined in a vessel, which was evacuated and purged with N2 three times. MeCN (25 ml) was added and the vessel was purged with N2 and then heated at 80 C overnight. The mixture was diluted with DCM (20 ml) and filtered through Celite, washing with DCM (3 x 20 ml). The filtrate was concentrated in vacuo and the residue was purified by column chromatography (80 g cartridge, 0-25% EtOAc/isohexane) to afford the title compound (1.46 g, 3.91 mmol, 96% purity) as a cream powder. 1H NMR (400 MHz, DMSO- ) delta 7.74 (s, 1H), 7.62 - 7.50 (m, 2H), 7.15 - 7.10 (m, 2H), 1.41 - 1.22 (m, 21H), 1.17 - 1.10 (m, 4H).
6.5 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 2-methyltetrahydrofuran; at 80℃; for 8h;Inert atmosphere;	Compound B (2.4g, 7.7mmol) was dissolved in dry 2-methyltetrahydrofuran,Add bis(pinacolate) diboron (2.4g, 9.4mmol),Potassium acetate (1.5g, 15.4mmol),Pd(dppf)Cl2 (0.28g, 0.38mmol),After nitrogen substitution, the reaction was carried out at 80 degrees for 8 hours.The reaction solution was filtered through celite, and the filtrate was evaporated to dryness and washed with petroleum ether to obtain white solid product C (6.5g).That is (4-(1-((tert-butoxycarbonyl)amino)cyclopropyl)phenyl)boronic acid ester.

Reference： [1]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 3175; 3176
[2]Patent: US2012/108574,2012,A1 .Location in patent: Page/Page column 114
[3]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0391
[4]Patent: WO2016/102672,2016,A2 .Location in patent: Page/Page column 115
[5]Patent: CN111171065,2020,A .Location in patent: Paragraph 0020; 0024-0026; 0030-0032; 0036-0037

3
[ 345965-54-0 ]
[ 1313441-88-1 ]

Reference： [1]Patent: US2016/96834,2016,A1
[2]Patent: WO2016/102672,2016,A2
[3]Patent: US2012/108574,2012,A1

4
[ 1313441-88-1 ]
[ 1374262-88-0 ]
[ 1374261-40-1 ]

Reference： [1]Patent: US2012/108574,2012,A1

5
[ 1313441-88-1 ]
[ 1374262-88-0 ]
[ 1374263-34-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; ethyl acetate; at 80℃; for 18h;	Step 3: Preparation of tert-butyl {1-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclopropyl}carbamate A suspension of 3-bromo-2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine (50 mg) and tert-butyl {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl}carbamate (92 mg) and potassium phosphate (82 mg) and PdCl2(dppf)CH2Cl2 (11 mg) in dioxane (2.5 mL) and H2O (0.25 mL) was degassed for 5 min then stirred at 80 C. for 18 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (0-50% ethyl acetate in hexanes) gave the product (51 mg, 74%). 1HNMR (DMSO-d6) 400 MHz δ: 8.55 (s, 1H), 8.09-8.04 (m, 1H), 7.98-7.93 (m, 1H), 7.70 (br s, 1H), 7.48 (d, J=6.9 Hz, 2H), 7.39-7.06 (m, 10H), 6.94-6.87 (m, 1H), 6.78-6.65 (m, 1H), 1.44-1.08 (m, 13H). LCMS: 542 [M+H].

Reference： [1]Patent: US2012/108574,2012,A1 .Location in patent: Page/Page column 114

6
[ 1313441-88-1 ]
[ 1431551-97-1 ]
C₂₈H₃₃Cl₂FN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 80℃; for 4h;Inert atmosphere;	Example 21 N-((1 R,2S)-1 -(4'-(1-aminocyclopropyl)-[1 ,1 '-biphenyl]-4-yl)-3-fluoro- 1-hydroxypropan-2-yl)-2,2-dichloroacetamideA mixture of tert-butyl (1-(4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl)cyclopropyl)carbamate (252 mg, 0.7 mmol), 2,2-dichloro-1-((4S,5R)-4- (fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidin-3-yl)ethanone (250 mg, 0.56 mmol), CS2CO3 (365 mg, 1.12 mmol) in dioxane (4 mL) and water (1 mL) is bubbled with nitrogen gas for 2 minutes. Pd(PPh3)4 (64 mg, 0.056 mmol) is added and the resulting reaction mixture heated at 80C for 4 hours. After cooling to room temperature, the reaction is diluted with water (10 ml) and extracted with ethyl acetate (3x 10 mL). Combined organic extracts are dried over Na2S04 and concentrated. Crude compound dissolved in DCM (3 mL) and stirred with TFA (0.6 mL) at room temperature for 1 hour. Reaction is diluted with toluene (10 mL) and concentrated to a syrup. Crude compound is basified slowly using saturated aq. NaHC03, saturated with NaCI, and extracted with ethyl acetate (3x 30 mL). Combined extracts dried over Na2S04 and concentrated. Solid dissolved in DMF (2 mL) and purified using HPLC eluting from 5 to 95% water/ acetonitrile to give the title compound (90 mg): 1 HNMR (400 MHz,DMSO-de) ?: 1.16-1.28 (m, 2H), 1.31 -1.41 (m, 2H), 4.15-4.36 (m, 1.5 H), 4.38- 4.47 (m, 0.5H) 4.55-4.62 (m, 0.5H), 4.65-4.74(m, 0.5H), 4.90 (bs, 1 H) 5.98 (bs, 1 H), 6.54 (bs, 1 H), 7.41-7.53 (m, 4H), 7.64 (d, 2H, J=8.0Hz), 7.72 (d, 2H, J=8.0 Hz), 8.63 (d, 1 H, J= 8Hz), 8.66-8.79 (bs, 3H), m/z (CI) 41 1 [M+1].

Reference： [1]Patent: WO2013/57619,2013,A1 .Location in patent: Page/Page column 30

7
[ 1313441-88-1 ]
[ 1431551-97-1 ]
[ 1431551-84-6 ]

Reference： [1]Patent: WO2013/57619,2013,A1

8
[ 1313441-88-1 ]
[ 6980-08-1 ]
C₁₉H₂₂N₄O₄ [ No CAS ]