[ CAS No. 919347-67-4 ]

Name: 919347-67-4|(6-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyridin-3-yl)boronic acid|98%
Brand: Ambeed
SKU: A500470
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Quality Control of [ 919347-67-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 919347-67-4 ]

CAS No. :	919347-67-4	MDL No. :	MFCD09952037
Formula :	C₁₄H₂₂BN₃O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SYZMMRYQYWCLNC-UHFFFAOYSA-N
M.W :	307.15 g/mol	Pubchem ID :	53216586
Synonyms :

Safety of [ 919347-67-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 919347-67-4 ]

* 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 [ 919347-67-4 ]
Downstream synthetic route of [ 919347-67-4 ]

[ 919347-67-4 ] Synthesis Path-Upstream 1~1

1
[ 73183-34-3 ]
[ 153747-97-8 ]
[ 919347-67-4 ]
[ 496786-98-2 ]

Reference： [1] Patent: WO2015/88045, 2015, A1, . Location in patent: Paragraph 0239
[2] Patent: US2017/8885, 2017, A1, . Location in patent: Paragraph 0656; 0658
[3] Patent: WO2017/38909, 2017, A1, . Location in patent: Paragraph 0308; 0309; 0311

[ 919347-67-4 ] Synthesis Path-Downstream 1~19

1
[ 860625-21-4 ]
[ 919347-67-4 ]
3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[6-(1-piperazinyl)-3-pyridinyl]-1H-indole-7-carboxamide [ No CAS ]
[ 919347-05-0 ]

Yield	Reaction Conditions	Operation in experiment
44%	With caesium carbonate In 1,4-dioxane; water; ethyl acetate	135 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[6-(1-piperazinyl)-3-pyridinyl]-1H-indole-7-carboxamide trifluoroacetate Example 135 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[6-(1-piperazinyl)-3-pyridinyl]-1H-indole-7-carboxamide trifluoroacetate To a solution of 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (100 mg, 0.241 mmol) in dioxane (1.0 mL) and H2O (0.8 mL) was added cesium carbonate (314 mg, 0.964 mmol), and [6-(4-[(1,1-dimethylethyl)oxy]carbonyl}-1-piperazinyl)-3-pyridinyl]boronic acid (297 mg, 0.964 mmol). The reaction mixture was stirred before addition of tetrakis(triphenylphosphine)palladium(0) (28 mg, 0.024 mmol). The reaction was heated in a microwave at 160° C. for 20 min. Mixture was concentrated and taken up in EtOAc (10 mL) and H2O (5.0 mL). Compound was purified by Gilson Preparatory HPLC to give 129 mg of 1,1-dimethylethyl 4-(5-{7-(aminocarbonyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indol-5-yl}-2-pyridinyl)-1-piperazinecarboxylate and 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[6-(1-piperazinyl)-3-pyridinyl]-1H-indole-7-carboxamide (44%).
44%	With caesium carbonate In 1,4-dioxane; water at 160℃; for 0.333333h; Microwave irradiation;	135 Example 135: 3-ri-(ethylsulfonyl)-4-piperidinvn-5-r6-(1-piperazinyl)-3-pyridinvn-1 H- indole-7-carboxamide trifluoroacetate; To a solution of 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1 H-indole-7-carboxamide (100 mg, 0.241 mmol) in dioxane (1.0 mL) and H2O (0.8 mL) was added cesium carbonate (314 mg, 0.964 mmol), and [6-(4-[(1 ,1-dimethylethyl)oxy]carbonyl}-1 -piperazinyl)-3- pyridinyl]boronic acid (297 mg, 0.964 mmol). The reaction mixture was stirred before addition of tetrakis(triphenylphosphine)palladium(0) (28 mg, 0.024 mmol). The reaction EPO was heated in a microwave at 160s C for 20 min. Mixture was concentrated and taken up in EtOAc (10 mL) and H2O (5.0 mL). Compound was purified by Gilson Preparatory HPLC to give 129 mg of 1 ,1-dimethylethyl 4-(5-{7-(aminocarbonyl)-3-[1-(ethylsulfonyl)-4- piperidinyl]-1 H-indol-5-yl}-2-pyridinyl)-1 -piperazinecarboxylate and 3-[1 -(ethylsulfonyl)-4- piperidinyl]-5-[6-(1 -piperazinyl)-3-pyridinyl]-1 H-indole-7-carboxamide (44%).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2009/143372, 2009, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2007/5534, 2007, A2 Location in patent: Page/Page column 164-165

2
[ 919347-67-4 ]
[ 102-92-1 ]
C₁₈H₂₀BN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (6-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyridin-3-yl)boronic acid With trifluoroacetic acid In dichloromethane at 20℃; Stage #2: Cinnamoyl chloride With triethylamine In tetrahydrofuran at 20℃;

Reference： [1]Current Patent Assignee: THE JOHNS HOPKINS UNIVERSITY - WO2005/63774, 2005, A1 Location in patent: Page/Page column 30

3
[ 919347-67-4 ]
[ 1611001-38-7 ]
[ 1611001-41-2 ]

Yield	Reaction Conditions	Operation in experiment
54.6%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	104 Example 104: t-Butyl 4-(5-(8-cyano-6-(6-methylpyridin-3-yl)imidazo[1 ,2-a] pyridin-3-yl) pyridin-2- yl)piperazine-1 -carboxylate The compound of example 1 00 (0.2 g, 0.639 mmol) was treated with 6-(4-(t- butoxycarbonyl)piperazin-1 -yl)pyridin-3-ylboronic acid (0.235 g, 0.766 mmol) in DMF (5 ml_) in presence of [1 , 1 '-bis(diphenylphosphino)ferrocene]dichloro palladium(l l) complex with dichloromethane (0.01 565 g, 0.01 9 mmol) and sodium carbonate (0.1 35 g, 1 .277 mmol) solution in 1 ml_ of water according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.1 73 g (54.6 %) ; 1 H NMR (300 MHz, DMSO-d6): δ 1 .43 (s, 9H, 3CH3), 2.50 (s, 3H, CH3), 3.45 (s, 4H, 2CH2), 3.61 (s, 4H, 2CH2), 7.01 (d, 1 H, J = 8.7 Hz, Ar), 7.36 (d, 1 H, J = 8.1 Hz, Ar), 7.88 (s, 1 H, Ar), 7.95 (d, 1 H, J = 9.0 Hz, Ar), 8.08 (d, 1 H, J = 8.1 Hz, Ar), 8.43 - 8.47 (m, 2H, Ar), 8.84 (s, 2H, Ar) ; MS (ES+) : m/e 496.2 (M+1 ).

Reference： [1]Current Patent Assignee: PIRAMAL ENTERPRISES LIMITED - WO2014/80241, 2014, A1 Location in patent: Page/Page column 70

4
[ 919347-67-4 ]
[ 1611001-19-4 ]
[ 1610999-83-1 ]

Yield	Reaction Conditions	Operation in experiment
34%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	60 Example 60: 3- t-Butyl 4-(5-(6-(2,6-dimethylpyridin-3-yl)-8-methylimidazo [1 ,2-a]pyridin-3-yl) pyridin-2-yl)piperazine-1 -carboxylate The compound of example 59 (0.7 g, 2.21 mmol) was treated with (6-(4-(t- butoxycarbonyl)piperazin-1 -yl)pyridin-3-yl)boronic acid (0.748 g, 2.43 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.029 g, 0.035 mmol) and sodium carbonate (0.35 g, 3.32 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.375 g (34 %) ; 1 H NMR (DMSO-d6, 300 MHz): δ 1 .42 (s, 9H, 3CH3), 2.42 (s, 3H, CH3), 2.48 (s, 3H, CH3), 2.56 (s, 3H, CH3), 3.42 (s, 4H, 2CH2), 3.56 (s, 4H, 2CH2), 6.97 (d, 1 H, J=9.0 Hz, Ar), 7.1 2-7.1 5 (m, 2H, Ar), 7.58-7.61 (m, 1 H, Ar), 7.68 (s, 1 H, Ar), 7.83-8.87 (dd, 1 H, J=8.7, 2.1 Hz, Ar), 8.1 0 (s, 1 H, Ar), 8.38 (d, 1 H, J=2.1 Hz, Ar); MS (ES+) : m/e 499 (M+1 ).

Reference： [1]Current Patent Assignee: PIRAMAL ENTERPRISES LIMITED - WO2014/80241, 2014, A1 Location in patent: Page/Page column 54

5
[ 18791-75-8 ]
[ 919347-67-4 ]
(Z)-tert-butyl-4-(4-(5-((6-methyl-3,4-dioxo-4,5-dihydrofuro-[3,4-c]pyridin-1(3H)-ylidene) methyl) thiophen-3-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water / 14.25 h / 100 °C / Inert atmosphere 2: piperidine / ethanol / 16 h / 80 °C / Inert atmosphere; Reflux

Reference： [1]Bathula, Chandramohan; Mamidala, Rajinikanth; Thulluri, Chiranjeevi; Agarwal, Rahul; Jha, Kunal Kumar; Munshi, Parthapratim; Adepally, Uma; Singh, Ashutosh; Chary, M. Thirumala; Sen, Subhabrata [RSC Advances, 2015, vol. 5, # 110, p. 90374 - 90385]

6
[ 18791-75-8 ]
[ 919347-67-4 ]
tert-butyl 4-(5-(5-formylthiophen-3-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 14.25h; Inert atmosphere;

7
[ 73183-34-3 ]
[ 153747-97-8 ]
[ 919347-67-4 ]
[ 496786-98-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 20.25h;Inert atmosphere;	A mixture of 1-11 (4.30 g, 12.57 mmol) , bis (pinacolato) diboron (3.82 g 15.07 mmol) and KOAc (2.94 g, 37.69 mmol) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1- bis (diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (0.307 g, 0.376 mmol), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100°C for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL) , followed by extraction with ethyl acetate (50 mL x 3) . The combined organic layers were washed with brine (50 mL) , dried over anhydrous Na2SC> and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50percent EtOAc in hexanes to give the desired product Intermediate 1- XIII as a mixture of minor boronate ester together with major boronic acid . (4.8 g, crude yield 98percent) as a yellow solid; LCMS (for boronate ester) : m/z 390.2 [M+l]; LCMS (for boronic acid) : m/z 308.1 [M+l] .
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere;	Step II: tert-butyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]piperazine-1-carboxylate (Intermediate 1-XIII) A mixture of 1-11 (4.30 g, 12.57 mmol), bis(pinacolato)diboron (3.82 g, 15.07 mmol) and KOAc (2.94 g, 37.69 mmol) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1-bis(diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (0.307 g, 0.376 mmol), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100° C. for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate (50 mL*3). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50percent EtOAc in hexanes to give the desired product Intermediate 1-XIII as a mixture of minor boronate ester together with major boronic acid (4.8 g, crude yield 98percent) as a yellow solid; LCMS (for boronate ester): m/z 390.2 [M+1]; LCMS (for boronic acid): m/z 308.1 [M++1].
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere;	A mixture of 1?28 (4.30 g, 12.57 rnmol), bis(pinacolato)diboron (3.82 g, 15.07 mmcl) and KOAc (2.94 g, 37.69 mmcl) in 1,4?dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1- bis (diphenylphosphino) ferrocenepalladium(II) dichloridedichloromethane complex (0.307 g, 0.376 mmcl), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100°C for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate(50 mL x 3) . The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50percent EtOAc in hexanes to give the desired product Intermediate 1-CII as a mixture of minor boronate ester together with major boronic acid (4.8 g, crude yield 98percent) as a yellow solid; IJCMS (for boronate ester): m/z 390.2 [M+1]; LCMS (for boronic acid): m/z 308.1 [M+1].

Reference： [1]Patent: WO2015/88045,2015,A1 .Location in patent: Paragraph 0239
[2]Patent: US2017/8885,2017,A1 .Location in patent: Paragraph 0656; 0658
[3]Patent: WO2017/38909,2017,A1 .Location in patent: Paragraph 0308; 0309; 0311

8
[ 919347-67-4 ]
6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-yltrifluoromethane sulfonate [ No CAS ]
tert-butyl 4-(5-(6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere; Sealed tube;	311 tert-Butyl 4-(5-(6-( i-methyl- 1H-pyrazol-4-yl)pyrazolo[ 1 ,5-a]pyridin-4-yl)pyridin-2- yl)piperazine- 1 -carboxylate tert-Butyl 4-(5-(6-( i-methyl- 1H-pyrazol-4-yl)pyrazolo[ 1 ,5-a]pyridin-4-yl)pyridin-2- yl)piperazine- 1 -carboxylate trifluoromethanesulfonate (Intermediate P7; 750 mg, 2.17 mmol), (6-(4-(tert- butoxycarbonyl)piperazin- 1 -yl)pyridin-3 -yl)boronic acid (998 mg, 3.25 mmol), Pd(PPh3)4 (250 mg, 0.2 17 mmol) and 2 M Na2CO3(aq) (5.42 mL, 10.8 mmol) were combined in dioxane (20 mL). The resulting reaction mixture was sparged with nitrogen, then sealed and heated at 100 °C overnight. After cooling to ambient temperature the reaction mixture was diluted with water (10 mL) and extracted with several portions of DCM in a PS frit. The combined organic extracts were concentrated in vacuo and purified by silica chromatography (10-100% EtOAc/hexanes) to afford the title compound (826 mg, 83% yield). MS (apci) m/z = 460.1 (M+H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2017/11776, 2017, A1 Location in patent: Paragraph 001297; 001298; 001299

9
[ 919347-67-4 ]
3-bromo-5-(methylsulfonyl)-4H-1,2,4-triazole [ No CAS ]
C₁₇H₂₄N₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In water; N,N-dimethyl-formamide at 100℃;

Reference： [1]Boezio, Alessandro A.; Andrews, Kristin; Boezio, Christiane; Chu-Moyer, Margaret; Copeland, Katrina W.; DiMauro, Erin F.; Foti, Robert S.; Fremeau, Robert T.; Gao, Hua; Geuns-Meyer, Stephanie; Graceffa, Russell F.; Gunaydin, Hakan; Huang, Hongbing; La, Daniel S.; Ligutti, Joseph; Moyer, Bryan D.; Peterson, Emily A.; Yu, Violeta; Weiss, Matthew M. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 11, p. 2103 - 2108]

10
[ 919347-67-4 ]
(2RS)-2-(6-bromo-7-chloroindazol-2-yl)-2-phenyl-N-thiazol-2-ylacetamide [ No CAS ]
tert-butyl 4-[5-[7-chloro-2-[(1RS)-2-oxo-1-phenyl-2-(thiazol-2-ylamino)ethyl]indazol-6-yl]-2-pyridyl]piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,4-dioxane; water at 90℃; for 25h;	8.5 Step 5: tert-Butyl 4-r5-r7-chloro-2-r(lRS)-2-oxo-l-phenyl-2-(thiazol-2- ylamino)ethyllindazol-6-yll-2-pyridyllpiperazine-l-carboxylate (2RS)-2-(6-Bromo-7-chloro-indazol-2-yl)-2-phenyl-N-thiazol-2-yl-acetamide (Example 8, step 4) (438 mg, 0.959 mmol) and (6-(4-(tert-butoxycarbonyl)piperazin-l-yl)pyridin-3- yl)boronic acid (CAS 919347-67-4) (353 mg, 1.15 mmol, 1.2 equiv.) were dissolved in 6.0 ml of dioxane , 2.0 ml of water and 2 M aq. Na2C03-solution (1.44 ml, 2.88 mmol, 3 equiv.). Dichloro[l,l'-bis(diphenylphosphino)ferrocene]-palladium(II), complex with dichloromethane (54.8 mg, 0.0671 mmol, 0.07 equiv.) was added and the reaction mixture was stirred at 90°C for 25 hours. The reaction mixture was cooled to room temperature and then extracted with ethyl acetate and saturated NaHCOs-solution. The aqueous layer was back-extracted with ethyl acetate. The organic layers were washed with water and brine. The organic layers were combined, dried over sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with an ethyl acetate:heptane 0: 100 to 100:0 gradient. The desired tert-butyl 4-[5-[7-chloro-2-[(lRS)-2-oxo-l-phenyl-2-(thiazol-2- ylamino)ethyl]indazol-6-yl]-2-pyridyl]piperazine-l-carboxylate (128 mg, 21 % yield) was obtained as a light yellow foam, MS: m/e = 630.4/632.4 (M+H+).

Reference： [1]Current Patent Assignee: C4 THERAPEUTICS INC; ROCHE HOLDING AG - WO2018/115218, 2018, A1 Location in patent: Page/Page column 33-34

11
[ 919347-67-4 ]
(2RS)-2-(6-bromo-7-chloroindazol-2-yl)-2-phenyl-N-thiazol-2-ylacetamide [ No CAS ]
(2RS)-2-[7-chloro-6-(6-piperazin-1-yl-3-pyridyl)indazol-2-yl]-2-phenyl-N-thiazol-2-ylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,4-dioxane / 25 h / 90 °C 2: hydrogenchloride / methanol; dichloromethane; 1,4-dioxane / 16 h / 20 °C

Reference： [1]Current Patent Assignee: C4 THERAPEUTICS INC; ROCHE HOLDING AG - WO2018/115218, 2018, A1

12
[ 919347-67-4 ]
(±)-(5-bromo-2,4-dimethoxypyridin-3-yl)(4-isopropylphenyl)methanol [ No CAS ]
(±)-tert-butyl 4-(5'-(hydroxy(4-isopropylphenyl)methyl)-4',6'-dimethoxy-[3,3'-bipyridin]-6-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; toluene for 16h; Reflux; Inert atmosphere; Schlenk technique;	General procedure II (GP II): Suzuki coupling with C3-functionalized 5-bromo aromatic compounds General procedure: The functionalized 5-bromopyridine (1.0 eq.) was dissolved together with the corresponding boronic acid or a corresponding boronic acid ester (2.0 eq.), tetrakis(tri-phenylphosphine)palladium (0) (10 mol%) and 1,1'bis(diphenylphosphino) ferrocene (20 mol%) in a mixture of toluene/ethanol (4:1, 0.05 M based on the 5-bromopyridine) and sodium carbonate solution (aq., 2 M, 70% by volume of the organic solvents) was added. The reaction mixture was degassed and refluxed (oil bath temperature 110 °C) for 16-20 h. After bringing the reaction mixture to rt, it was diluted with EtOAc and separated from the aqueous layer. The organic layer was washed with sat. sodium chloride solution (aq.), dried over anhydrous magnesium sulfate and filtered over celite. The filtrate was concentrated in vacuo and the crude product was purified by means of flash chromatography on silica gel.

Reference： [1]Robke, Lucas; Rodrigues, Tiago; Schröder, Peter; Foley, Daniel J.; Bernardes, Gonçalo J.L.; Laraia, Luca; Waldmann, Herbert [Tetrahedron, 2018, vol. 74, # 35, p. 4531 - 4537]

13
[ 919347-67-4 ]
[ 201230-82-2 ]
[ 257887-58-4 ]
tert-butyl 4-(5-(2,2-difluoro-4-(triisopropylsilyl)but-3-ynoyl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With (1,2-dimethoxyethane)dichloronickel(II); water; potassium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine In 1,4-dioxane at 65℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Zhao, Hai-Yang; Gao, Xing; Zhang, Shu; Zhang, Xingang [Organic Letters, 2019, vol. 21, # 4, p. 1031 - 1036]

14
[ 919347-67-4 ]
N-(5-bromo-4-fluoro-2-((3S,5R)-3,4,5-trimethylpiperazin-1-yl)phenyl)-6-oxo-4-(trifluoromethyl)-1,6-dihydropyridine-3-carboxamide [ No CAS ]
[ 76-05-1 ]
(x)C₂HF₃O₂*C₂₉H₃₃F₄N₇O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: (6-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyridin-3-yl)boronic acid; N-(5-bromo-4-fluoro-2-((3S,5R)-3,4,5-trimethylpiperazin-1-yl)phenyl)-6-oxo-4-(trifluoromethyl)-1,6-dihydropyridine-3-carboxamide With (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); sodium carbonate; XPhos In 1,4-dioxane; water at 120℃; for 1h; Microwave irradiation; Stage #2: trifluoroacetic acid In dichloromethane at 20℃; for 1h;	147 Example 147: Synthesis of Intermediate 36 To a solution of Intermediate 35 (WO2017147700A1) (505 mg, 1 mmol) and (6-(4-(tert- butoxycarbonyl)piperazin-1-yl)pyridin-3-yl)boronic acid (924 mg, 3 mmol, 3.0 euqiv) in 8 mL of 1,4-dioxane / H2O (5 : 3) were added sodium carbonate (1060 mg, 10 mmol, 10 equiv), XPhos (95.2 mg, 0.2 mmol, 0.2 equiv), and XPhos Pd G2 (157.4 mg, 0.2 mmol, 0.2 equiv). The reaction was heated to 120 oC for 1 h under Microwave. The solvent was removed and purified by reverse phase ISCO (10%- 100% methanol / 0.1% TFA in H2O) to afford product as white solid. This product was dissolved in DCM (10 mL) and TFA (10 mL). The resulting mixture was stirring for 1 h. Then, it was concentrated and purified by reverse phase ISCO (10%- 100% methanol / 0.1% TFA in H2O) to afford Intermediate 36 as white solid in TFA salt form (463.4 mg, yield 79%).1H NMR (600 MHz, CD3OD) d 8.32 (d, J = 2.2 Hz, 1H), 8.19 (dd, J = 9.2, 2.3 Hz, 1H), 8.07- 7.92 (m, 2H), 7.40 (d, J = 9.4 Hz, 1H), 7.20 (d, J = 11.8 Hz, 1H), 6.89 (s, 1H), 4.01 (t, J = 5.3 Hz, 4H), 3.62- 3.53 (m, 2H), 3.49- 3.39 (m, 4H), 3.35 (d, J = 12.7 Hz, 2H), 3.01 (dd, J = 13.4, 11.0 Hz, 2H), 2.97 (s, 3H), 1.43 (d, J = 6.4 Hz, 6H). HRMS (m/z) for C29H34F4N7O2+ [M + H]+: calculated 588.2705, found 588.2732

Reference： [1]Current Patent Assignee: ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; UNIVERSITY OF NORTH CAROLINA SYSTEM - WO2019/246570, 2019, A1 Location in patent: Page/Page column 205-206

15
[ 919347-67-4 ]
(x)C₂HF₃O₂*C₅₅H₆₅F₄N₁₁O₇S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium carbonate; XPhos; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)) / 1,4-dioxane; water / 1 h / 120 °C / Microwave irradiation 1.2: 1 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; UNIVERSITY OF NORTH CAROLINA SYSTEM - WO2019/246570, 2019, A1

16
[ 919347-67-4 ]
(x)C₂HF₃O₂*C₅₉H₇₂F₄N₁₂O₉S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium carbonate; XPhos; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)) / 1,4-dioxane; water / 1 h / 120 °C / Microwave irradiation 1.2: 1 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / dichloromethane / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; UNIVERSITY OF NORTH CAROLINA SYSTEM - WO2019/246570, 2019, A1

17
[ 919347-67-4 ]
(x)C₂HF₃O₂*C₃₃H₃₇F₄N₇O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium carbonate; XPhos; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)) / 1,4-dioxane; water / 1 h / 120 °C / Microwave irradiation 1.2: 1 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; UNIVERSITY OF NORTH CAROLINA SYSTEM - WO2019/246570, 2019, A1

18
[ 919347-67-4 ]
5-bromo-1-(2,6-dichlorobenzoyl)-3-[3-[[ethyl(methyl)sulfamoyl]amino]-2,6-difluorobenzoyl]pyrrolo[2,3-b]pyridine [ No CAS ]
C₃₈H₃₇Cl₂F₂N₇O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; potassium carbonate; triphenylphosphine In ethylene glycol dimethyl ether; lithium hydroxide monohydrate Reflux;	a General procedure II: a) Suzuki cross coupling, b) 2,6-dichlorobenzoyl deprotection, c) N-BOC deprotection General procedure: a) To a mixture of an appropriately selected sulfamoyl intermediate (1 eq) or sulfonamide intermediate (1 eq), a boronic acid which is either commercially available or prepared by methods known in the art (1.5 eq) and potassium carbonate (3 eq) in 1, 2-dimethoxy ethane / water (4:1, 0.1- 0.2 M), which has been purged with argon, are consecutively added triphenylphosphine (0.1 eq) and palladium(II)acetate (0.05 eq). The mixture is stirred at reflux for 3-20 h. After cooling to room temperature the reaction mixture is partitioned between an organic solvent such as ethyl acetate or dichloromethane and 1M sodium bicarbonate solution. The layers are separated. The aqueous layer is extracted with one or two portions of organic solvent. The combined organic layers are washed with one portion of brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by flash-chromatography gives the desired intermediate 1001.
	With palladium diacetate; potassium carbonate; triphenylphosphine In ethylene glycol dimethyl ether; lithium hydroxide monohydrate Inert atmosphere; Reflux;	General procedure VII: a) Suzuki cross coupling, b) 2,6-dichlorobenzoyl deprotection, c) N-BOC deprotection General procedure: a) To a mixture of a sulfamoyl intermediate of intermediate formula XVI-a (1 eq) or a sulfonamide intermediate of intermediate formula XVI -b (1 eq), a boronic acid intermediate of intermediate formula XVII which is either commercially available or prepared by methods known in the art (1.5 eq) and potassium carbonate (3 eq) in 1,2- dimethoxyethane / water (4:1, 0.1 -0.2 M), which has been purged with argon, are consecutively added triphenylphosphine (0.1 eq) and palladium(II)acetate (0.05 eq). The mixture is stirred at reflux for 3-20 h. After cooling to room temperature the reaction mixture is partitioned between an organic solvent such as ethyl acetate or dichloromethane and 1M sodium bicarbonate solution. The layers are separated. The aqueous layer is extracted with one or two portions of organic solvent. The combined organic layers are washed with one portion of brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by flash-chromatography gives an intermediate of intermediate formula XVIII.

Reference： [1]Current Patent Assignee: C4 THERAPEUTICS INC; ROCHE HOLDING AG - WO2021/255213, 2021, A1 Location in patent: Page/Page column 32; 33
[2]Current Patent Assignee: C4 THERAPEUTICS INC; ROCHE HOLDING AG - WO2021/255212, 2021, A1 Location in patent: Page/Page column 580-582

19
[ 919347-67-4 ]
(3-amino-2-bromophenyl)-[5-bromo-1-(2,6-dichlorobenzoyl)pyrrolo[2,3-b]pyridin-3-yl]methanone [ No CAS ]
tert-butyl 4-(5-(3-(3-amino-2-bromobenzoyl)-1-(2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With palladium diacetate; potassium carbonate; triphenylphosphine In ethylene glycol dimethyl ether; lithium hydroxide monohydrate at 90℃; for 15h; Inert atmosphere;	d) tert-Butyl 4-(5-(3-(3-amino-2-bromobenzoyl)-l-(2, 6-dichlorobenzoyl)-lH-pyrrolo[2, 3- b]pyridin-5-yl)pyridin-2-yl)piperazine-l-carboxylate To a mixture of (3-(3-amino-2-bromobenzoyl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-l-yl)(2,6- dichlorophenyl)methanone (1 g, 1.76 mmol, Eq: 1), (6-(4-(tert-butoxycarbonyl)piperazin-l- yl)pyridin-3-yl)boronic acid (595 mg, 1.94 mmol, Eq: 1.1) and potassium carbonate (730 mg, 5.28 mmol, Eq: 3) in 1,2-dimethoxy ethane (14.1 ml) and water (3.52 ml) were added triphenylphosphine (92.3 mg, 352 μmol, Eq: 0.2) and palladium (II) acetate (39.5 mg, 176 μmol, Eq: 0.1). The RM was purged with Argon by two vacuo / Argon cycles, then heated to 90 °C and stirred for 15 h. The reaction mixture was partitioned between ethyl acetate (50 ml) and water (30 ml). The layers were separated. The aqueous layer was extracted with two 50-ml portions of ethyl acetate. The combined organic layers were washed with one 40 -ml portion of brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography with n-heptane / ethyl acetate as eluent. The solid obtained from the flash chromatography was triturated in methanol (10 ml). The precipitate was collected by filtration to give the title compound (1.06 g, 81%) as orange solid. MS m/e: 751.1 ([M+H+]+).
81%	With palladium diacetate; potassium carbonate; triphenylphosphine In ethylene glycol dimethyl ether; lithium hydroxide monohydrate at 90℃; for 15h; Inert atmosphere;	d) tert-Butyl 4-(5-(3-(3-amino-2-bromobenzoyl)-l-(2, 6-dichlorobenzoyl)-lH-pyrrolo[2, 3- b]pyridin-5-yl)pyridin-2-yl)piperazine-l-carboxylate To a mixture of (3-(3-amino-2-bromobenzoyl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-l-yl)(2,6- dichlorophenyl)methanone (1 g, 1.76 mmol, Eq: 1), (6-(4-(tert-butoxycarbonyl)piperazin-l- yl)pyridin-3-yl)boronic acid (595 mg, 1.94 mmol, Eq: 1.1) and potassium carbonate (730 mg, 5.28 mmol, Eq: 3) in 1,2-dimethoxy ethane (14.1 ml) and water (3.52 ml) were added triphenylphosphine (92.3 mg, 352 μmol, Eq: 0.2) and palladium (II) acetate (39.5 mg, 176 μmol, Eq: 0.1). The RM was purged with Argon by two vacuo / Argon cycles, then heated to 90 °C and stirred for 15 h. The reaction mixture was partitioned between ethyl acetate (50 ml) and water (30 ml). The layers were separated. The aqueous layer was extracted with two 50-ml portions of ethyl acetate. The combined organic layers were washed with one 40 -ml portion of brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography with n-heptane / ethyl acetate as eluent. The solid obtained from the flash chromatography was triturated in methanol (10 ml). The precipitate was collected by filtration to give the title compound (1.06 g, 81%) as orange solid. MS m/e: 751.1 ([M+H+]+).

Reference： [1]Current Patent Assignee: C4 THERAPEUTICS INC; ROCHE HOLDING AG - WO2021/255212, 2021, A1 Location in patent: Page/Page column 580; 596-597
[2]Current Patent Assignee: C4 THERAPEUTICS INC; ROCHE HOLDING AG - WO2021/255212, 2021, A1 Location in patent: Page/Page column 580; 596-597

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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. 919347-67-4 ]

Quality Control of [ 919347-67-4 ]

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[ 919347-67-4 ] Synthesis Path-Upstream 1~1

[ 919347-67-4 ] Synthesis Path-Downstream 1~19

Related Functional Groups of [ 919347-67-4 ]

Organoboron

Amides

Related Parent Nucleus of [ 919347-67-4 ]

Pyridines

Piperazines

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[ 919347-67-4 ]

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[ 919347-67-4 ]