[ CAS No. 1215387-58-8 ] {[proInfo.proName]}

Name: 1215387-58-8|5-Bromo-1H-pyrrolo[2,3-c]pyridine|98%
Brand: Ambeed
SKU: A113356
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Quality Control of [ 1215387-58-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1215387-58-8 ]

Product Details of [ 1215387-58-8 ]

CAS No. :	1215387-58-8	MDL No. :	MFCD12024306
Formula :	C₇H₅BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HIYAJEAFUVCOFA-UHFFFAOYSA-N
M.W :	197.03	Pubchem ID :	53443442
Synonyms :

Calculated chemistry of [ 1215387-58-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.79
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.56
Log Po/w (XLOGP3) :	2.0
Log Po/w (WLOGP) :	2.33
Log Po/w (MLOGP) :	1.07
Log Po/w (SILICOS-IT) :	2.75
Consensus Log Po/w :	1.94

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.99
Solubility :	0.203 mg/ml ; 0.00103 mol/l
Class :	Soluble
Log S (Ali) :	-2.23
Solubility :	1.16 mg/ml ; 0.0059 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.77
Solubility :	0.0337 mg/ml ; 0.000171 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 1215387-58-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1215387-58-8 ]

* 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 [ 1215387-58-8 ]
Downstream synthetic route of [ 1215387-58-8 ]

[ 1215387-58-8 ] Synthesis Path-Upstream 1~4

1
[ 1268816-53-0 ]
[ 1215387-58-8 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: at 20 - 70℃; for 2 h;	Step 4: 5-bromo-lH-pyrrolo[2,3-c]pyridineTo the solution of 2-(2-bromo-5-nitropyridin-4-yl)-N,N- dimethylethenamine (62 mg, 0.23 mmol) in AcOH (2 mL), iron (127 mg, 2.28 mmol) was added at room temperature and the mixture was heated at 70 °C for 2 hours. The mixture was cooled, poured into EtOAc (30 mL), filtered through Celite. The filtration was washed with 5percent NaHC0₃ solution, water and brine, dried over Na₂S0₄. The solvent was concentrated in vacuo to the desired product (25 mg, 56percent).1H NMR (CDC1₃): δ 9.42 (1H, br), 8.60 (1H, s), 7.74 (1H, s), 7.47 (1H, d, / = 2.8 Hz), 6.54 (1H, d, / = 2.8 Hz).
39%	Stage #1: With lithium aluminium tetrahydride; titanium tetrachloride In tetrahydrofuran at 20℃; for 0.916667 h; Inert atmosphere Stage #2: With ammonia In tetrahydrofuran	(2) 5-Bromo-1H-pyrrolo[2,3-c]pyridine Under N₂, titanium(IV) chloride (75 μL, 0.69 mmol) was added dropwise to tetrahydrofuran (2 mL) at 0°C, then lithium aluminium hydride (19 mg, 0.50 mmol) was portionwise added to this mixture and stirred for 15 minutes. To this was added dropwise a solution of 2-(2-bromo-5-nitropyridin-4-yl)-N,N-dimethylethenamine in tetrahydrofuran (1.5 mL) over 5 minutes, and the mixture was stirred at room temperature for 50 minutes. The reaction mixture was added 25percent ammonia solution (0.5 mL) slowly, and was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 2/3), to give the title compound as a pale yellow crystal (15 mg, yield 39percent). ¹H NMR (CDCl₃ 400 MHz): δ= 6.5-6.6 (1H, m), 7.42 (1H, t, J = 3 Hz), 7.73 (1H, s), 8.59 (1H, s), 8.63 (1H, br s).
11 g	at 70℃; for 2 h;	The crude product from above was dissolved in acetic acid (1000 mL), iron (78.0 g, 1400 mmol, 10 eq) was added at room temperature and the mixture was heated to 70° C. for 2 hr, filtered through a celite pad and concentrated under reduced pressure. The residue was basified with saturated NaHCO₃ solution solid and the resulting solid was collected by filtration. The crude product was purified by column chromatography (100-200 silica gel) to give 5-bromo-1H-pyrrolo[2,3-c]pyridine as a brown solid (11.0 g). LCMS purity 98.8percent (ES⁺): m/z 197.24 (M+H⁺); tr=1.3 min

Reference： [1] Patent: WO2012/103806, 2012, A1, . Location in patent: Page/Page column 44
[2] Patent: EP2474540, 2012, A1, . Location in patent: Page/Page column 38
[3] Patent: US2017/298060, 2017, A1, . Location in patent: Paragraph 0089

2
[ 23056-47-5 ]
[ 1215387-58-8 ]

Reference： [1] Patent: EP2474540, 2012, A1,
[2] Patent: WO2012/103806, 2012, A1,
[3] Patent: US2017/298060, 2017, A1,

3
[ 695-34-1 ]
[ 1215387-58-8 ]

Reference： [1] Patent: WO2012/103806, 2012, A1,

4
[ 21901-40-6 ]
[ 1215387-58-8 ]

Reference： [1] Patent: WO2012/103806, 2012, A1,

[ 1215387-58-8 ] Synthesis Path-Downstream 1~87

1
[ 23056-47-5 ]
[ 1215387-58-8 ]

Reference： [1]Patent: EP2474540,2012,A1
[2]Patent: WO2012/103806,2012,A1
[3]Patent: US2017/298060,2017,A1

2
[ 1268816-53-0 ]
[ 1215387-58-8 ]

Yield	Reaction Conditions	Operation in experiment
56%		Step 4: 5-bromo-lH-pyrrolo[2,3-c]pyridineTo the solution of 2-(2-bromo-5-nitropyridin-4-yl)-N,N- dimethylethenamine (62 mg, 0.23 mmol) in AcOH (2 mL), iron (127 mg, 2.28 mmol) was added at room temperature and the mixture was heated at 70 C for 2 hours. The mixture was cooled, poured into EtOAc (30 mL), filtered through Celite. The filtration was washed with 5% NaHC03 solution, water and brine, dried over Na2S04. The solvent was concentrated in vacuo to the desired product (25 mg, 56%).1H NMR (CDC13): delta 9.42 (1H, br), 8.60 (1H, s), 7.74 (1H, s), 7.47 (1H, d, / = 2.8 Hz), 6.54 (1H, d, / = 2.8 Hz).
39%		(2) 5-Bromo-1H-pyrrolo[2,3-c]pyridine Under N2, titanium(IV) chloride (75 muL, 0.69 mmol) was added dropwise to tetrahydrofuran (2 mL) at 0C, then lithium aluminium hydride (19 mg, 0.50 mmol) was portionwise added to this mixture and stirred for 15 minutes. To this was added dropwise a solution of 2-(2-bromo-5-nitropyridin-4-yl)-N,N-dimethylethenamine in tetrahydrofuran (1.5 mL) over 5 minutes, and the mixture was stirred at room temperature for 50 minutes. The reaction mixture was added 25% ammonia solution (0.5 mL) slowly, and was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 2/3), to give the title compound as a pale yellow crystal (15 mg, yield 39%). 1H NMR (CDCl3 400 MHz): delta= 6.5-6.6 (1H, m), 7.42 (1H, t, J = 3 Hz), 7.73 (1H, s), 8.59 (1H, s), 8.63 (1H, br s).
11 g	With iron; acetic acid; at 70℃; for 2h;	The crude product from above was dissolved in acetic acid (1000 mL), iron (78.0 g, 1400 mmol, 10 eq) was added at room temperature and the mixture was heated to 70 C. for 2 hr, filtered through a celite pad and concentrated under reduced pressure. The residue was basified with saturated NaHCO3 solution solid and the resulting solid was collected by filtration. The crude product was purified by column chromatography (100-200 silica gel) to give 5-bromo-1H-pyrrolo[2,3-c]pyridine as a brown solid (11.0 g). LCMS purity 98.8% (ES+): m/z 197.24 (M+H+); tr=1.3 min

Reference： [1]Patent: WO2012/103806,2012,A1 .Location in patent: Page/Page column 44
[2]Patent: EP2474540,2012,A1 .Location in patent: Page/Page column 38
[3]Patent: US2017/298060,2017,A1 .Location in patent: Paragraph 0089

3
[ 695-34-1 ]
[ 1215387-58-8 ]

Reference： [1]Patent: WO2012/103806,2012,A1

4
[ 21901-40-6 ]
[ 1215387-58-8 ]

Reference： [1]Patent: WO2012/103806,2012,A1

5
[ 1215387-58-8 ]
C₁₂H₁₂BrN₃O [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1

6
[ 1215387-58-8 ]
C₁₁H₈BrN₅ [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1

7
[ 1215387-58-8 ]
C₁₆H₁₈BrN₅O [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1

8
[ 1215387-58-8 ]
C₁₁H₇BrClN₅ [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1

9
[ 1215387-58-8 ]
C₁₂H₁₀BrN₅ [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1

10
[ 1215387-58-8 ]
C₁₂H₁₀BrN₅ [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1

11
[ 1215387-58-8 ]
C₁₄H₁₄BrN₅O₂S [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1

12
[ 1215387-58-8 ]
C₁₆H₁₅N₅O [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1

13
[ 1215387-58-8 ]
C₁₂H₁₃BrN₂O [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1
[2]Patent: WO2016/62792,2016,A1

14
[ 1215387-58-8 ]
C₁₅H₁₈BrN₃O [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1
[2]Patent: WO2016/62792,2016,A1

15
[ 1215387-58-8 ]
C₁₄H₁₄BrN₅ [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1
[2]Patent: WO2016/62792,2016,A1

16
[ 1215387-58-8 ]
C₁₄H₁₃BrClN₅ [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1

17
[ 1215387-58-8 ]
C₁₆H₁₃BrN₂O₃S [ No CAS ]

Reference： [1]Patent: WO2014/174021,2014,A1

18
[ 1215387-58-8 ]
[ 75-36-5 ]
1-(5-bromo-1H-pyrrolo[2,3-c]pyridin-3-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.9%	With aluminum (III) chloride; In dichloromethane; at 0 - 20℃; for 0.25h;	To a stirred solution of <strong>[1215387-58-8]5-bromo-1H-pyrrolo[2,3-c]pyridine</strong> (500 mg, 2.53 mmol) in DCM (40mL), anhydrous AlCb (675 mg, 5.07 mmol) was added at 0C. The reaction mixture was stirred at RT for 15 minutes and then, acetyl chloride (396 mg, 5.07 mmol) was added. The reaction mixture was allowed to stirred at RT for 16h. The progress of the reaction was monitored by LCMS. The reaction mixture was concentrated under reduced pressure and poured into crushed ice and neutralized with 2N NaOH: The solid precipitated was filtered and dried under vacuum to afford the title compound (600mg, 98.90%). LC-MS (method 20): Rt = 1.61 min; m/z = 239.06 (M+H+).
87%		A stirred mixture of 5-bromo-lH-pyrrolo[2,3-c]pyridine (2.00 g, 10.2 mmol) in anhydrous DCM (65 ml) at ambient temperature was treated portionwise with aluminium chloride (2.70 g, 20.3 mmol). After stirring for 15 minutes, the mixture was treated dropwise with acetyl chloride (1.44 ml, 20.3 mmol) and the resulting mixture was stirred at ambient temperature for 24 hours. The mixture was treated cautiously with MeOH until no further effervescence was observed. The mixture was then concentrated in vacuo and the residue partitioned between 2.0 M aqueous sodium hydroxide and EtOAc. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was triturated with Et20 to afford the desired product (2.12 g, 87%). LCMS (Method B): Rt= 2.29 min, m/z [M+H]+ = 239/241

Reference： [1]Patent: WO2018/149986,2018,A1 .Location in patent: Paragraph 82
[2]Patent: WO2014/174021,2014,A1 .Location in patent: Page/Page column 113

19
[ 75-30-9 ]
[ 1215387-58-8 ]
C₁₀H₁₁BrN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		A stirred solution of 5-bromo-lH-pyrrolo[2,3-c]pyridine (2.0 g, 10.2 mmol) in anhydrous DMF (80 ml) under a nitrogen atmosphere at ambient temperature was treated portionwise with sodium hydride (0.49 g, 12.2 mmol, 60% in mineral oil). After stirring for 20 minutes, 2-iodopropane (1.1 ml, 11.2 mmol) was added dropwise and the resulting mixture stirred for 18 hours. The mixture was concentrated in vacuo and the residue partitioned between water and EtOAc. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with a mixture of EtOAc and pentane (1 :9 to 1 : 1 by volume), to afford the desired product as a brown oil (1.87 g, 77%). LCMS (Method C): Rt= 3.19 min, m/z [M+H]+ = 239/241
77%		A stirred solution of 5-bromo-lH-pyrrolo[2,3-c]pyridine (2.0 g, 10.2 mmol) in anhydrous DMF (80 ml) under a nitrogen atmosphere at ambient temperature was treated portionwise with sodium hydride (0.49 g, 12.2 mmol, 60% in mineral oil). After stirring for 20 minutes, 2-iodopropane (1.1 ml, 11.2 mmol) was added dropwise and the resulting mixture stirred for 18 hours. The mixture was concentrated in vacuo and the residue partitioned between water and EtOAc. The organic phase was washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with a mixture of EtOAc and pentane (1 :9 to 1 : 1 by volume), to afford the desired product as a brown oil (1.87 g, 77%). LCMS (Method C): Rt = 3.19 min, m/z [M+H]+ = 239/241

Reference： [1]Patent: WO2014/174021,2014,A1 .Location in patent: Page/Page column 120
[2]Patent: WO2016/62792,2016,A1 .Location in patent: Page/Page column 21

20
[ 1215387-58-8 ]
[ 7553-56-2 ]
5-bromo-3-iodo-1H-pyrrolo[2,3-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		Example A4a) Preparation of intermediate 6A stirred solution of 5-bromo-lH-pyrrolo[2,3-c]pyridine (4.00 g, 20.3 mmol) in DMF (150 ml) at ambient temperature was treated with potassium hydroxide (4.32 g, 77.2 mmol). After 10 minutes, iodine (5.67 g, 22.3 mmol) was added and the resulting mixture was stirred for 3 hours. The mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2S04and concentrated in vacuo. The residue was triturated with water, filtered and dried in vacuo to afford the desired product as an orange solid (5.71 g, 87%).LCMS (Method C): Rt= 3.23 min, m/z [M+H]+= 323/325.

Reference： [1]Patent: WO2015/44269,2015,A1 .Location in patent: Page/Page column 79; 80

21
[ 1215387-58-8 ]
C₁₅H₁₄N₄O [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

22
[ 1215387-58-8 ]
C₂₃H₂₇BrN₄O₃SSi [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

23
[ 1215387-58-8 ]
C₁₆H₂₁BrN₄OSi [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

24
[ 1215387-58-8 ]
5-bromo-1-methyl-3-(1-((2 (trimethylsilyl)ethoxyl)methyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

25
[ 1215387-58-8 ]
C₂₆H₃₈BrN₅O₃Si [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

26
[ 1215387-58-8 ]
C₂₁H₃₀BrN₅OSi [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

27
[ 1215387-58-8 ]
C₂₂H₃₂BrN₅OSi [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

28
[ 1215387-58-8 ]
C₁₇H₂₃BrN₄O₃SSi [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

29
[ 1215387-58-8 ]
C₂₅H₃₅BrN₄O₃Si [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

30
[ 1215387-58-8 ]
C₂₃H₃₃BrN₄O₂Si [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

31
[ 1215387-58-8 ]
C₂₃H₃₁BrF₃N₅OSi [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

32
[ 1215387-58-8 ]
C₂₈H₃₄N₄O₄SSi [ No CAS ]

Reference： [1]Patent: WO2015/44269,2015,A1

33
[ 1215387-58-8 ]
5-bromo-3-iodo-1H-pyrrolo[2,3-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		A stirred solution of 5-bromo-lH-pyrrolo[2,3-c]pyridine (2.22 g, 11.3 mmol) in DMF (30 ml) at ambient temperature was treated with potassium hydroxide (2.53 g, 45.1 mmol). After 10 minutes, iodine (3.15 g, 12.4 mmol) was added and the resulting mixture was stirred for 2 hours. The mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was triturated with water, filtered and dried in vacuo to afford the desired product as an orange solid (3.39 g, 93%). LCMS (Method C): Rt= 3.14 min, m/z [M+H]+ = 323/325.
93%		A stirred solution of <strong>[1215387-58-8]5-bromo-1H-pyrrolo[2,3-c]pyridine</strong> (2.22 g, 11.3 mmol) in DMF(30 ml) at ambient temperature was treated with potassium hydroxide (2.53 g, 45.1mmol). After 10 minutes, iodine (3.15 g, 12.4 mmol) was added and the resulting mixture was stirred for 2 hours. The mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was triturated with water to afford the desiredproduct as an orange solid (3.39 g, 93%).LCMS (Method C): R 3.14 mm, mlz [M+H] 323/325.
76%	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	To a stirred solution of <strong>[1215387-58-8]5-bromo-1H-pyrrolo[2,3-c]pyridine</strong> (2.0 g, 10.20 mmol) in DMF (30 mL) KOH (2.284 g, 40.8 mmol) and iodine (2.838 g, 1 .222 mmol) were added at 0C. The reaction mixture was stirred at RT for 2h. It was diluted with water and extracted with EtOAc. The combined organic layers were washed with water and brine solution. The organic layers were dried over anhydrous IStaSC , filtered and concentrated under reduced pressure. The crude compound was triturated with water, filtered and dried under vacuum to afford the title compound (2.5 g, 76%) as a pale yellow solid. LC-MS (method 18): Rt = 2.39 min; m/z = 320.84 (M-H+).

To a stirred solution of 5-bromo- 1 H-py rrolo [2, 3-c]pyrid i ne (1 g, 5.1 mmol) in DMF, KOH (0.86 g, 15.3 mmol) was added. It was stirred at rt for 20 minutes and then, iodine (1.54 g, 6.12 mmol) was added. The resulting mixture was stirred at rt for 16 h. The reaction mixture was evaporated under vacuum to get a crude residue. Crushed ice was added to the obtained crude residue and the precipitated solid was filtered, dried, and washed with diethylether to get 1 g (60 %) of a crude compound that was used for the next step without any further purification.LC-MS (method 6): Rt = 1.94 min; m/z = 323.01 (M+H+).

Reference： [1]Patent: WO2016/62789,2016,A1 .Location in patent: Page/Page column 54
[2]Patent: WO2016/62790,2016,A1 .Location in patent: Page/Page column 39
[3]Patent: WO2018/149986,2018,A1 .Location in patent: Page/Page column 86
[4]Patent: WO2019/110663,2019,A1 .Location in patent: Page/Page column 58

34
[ 1215387-58-8 ]
C₁₂H₁₂BrIN₂O₂ [ No CAS ]

Reference： [1]Patent: WO2016/62790,2016,A1

35
[ 1215387-58-8 ]
C₁₄H₁₃BrIN₅ [ No CAS ]

Reference： [1]Patent: WO2016/62792,2016,A1

36
[ 1215387-58-8 ]
C₂₂H₂₅N₇O₂ [ No CAS ]

Reference： [1]Patent: WO2016/62790,2016,A1

37
[ 1215387-58-8 ]
C₁₈H₁₆BrClN₆O₂ [ No CAS ]

Reference： [1]Patent: WO2016/62790,2016,A1

38
[ 1215387-58-8 ]
C₁₃H₈BrClN₆ [ No CAS ]

Reference： [1]Patent: WO2016/62790,2016,A1

39
[ 1215387-58-8 ]
C₁₇H₁₆BrClN₆O [ No CAS ]

Reference： [1]Patent: WO2016/62790,2016,A1

40
[ 1215387-58-8 ]
C₂₇H₃₀BrN₇O₄ [ No CAS ]

Reference： [1]Patent: WO2016/62790,2016,A1

41
[ 1215387-58-8 ]
C₁₇H₁₈BrN₇O [ No CAS ]

Reference： [1]Patent: WO2016/62790,2016,A1

42
[ 24424-99-5 ]
[ 1215387-58-8 ]
[ 1445856-13-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; In acetonitrile; at 20℃; for 0.75h;	To a suspension of 5-bromo-1H-pyrrolo [2,3-c] pyridine (10 g, 50.8 mmol) in acetonitrile (50 mL),4-Dimethylaminopyridine (0.62 g, 5.08 mmol) and di-tert-butyl dicarbonate (12.9 mL, 55.8 mmol) were added with stirring at room temperature for 45 minutes.Dilute the reaction with water (40 mL),Filter the reaction to obtain a filtered product,This was rinsed with water and dried in a vacuum oven at 60 C. to give the product (12.1 g, 80% yield).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3518 - 3524
[2]Patent: JP6557436,2019,B1 .Location in patent: Paragraph 0526; 0527; 0528

43
[ 1215387-58-8 ]
[ 166815-96-9 ]
tert-butyl 4-((5-bromo-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		Sodium hydride (60% suspension in mineral oil, 1.53 g, 38 mmol, 1.5 eq) was added to a stirred solution of <strong>[1215387-58-8]5-bromo-1H-pyrrolo[2,3-c]pyridine</strong> (5.0 g, 25.0 mmol, 1.0 eq) in DMF (50 mL) at 0 C. and stirring was continued at room temperature for 30 min. The mixture was again cooled to 0 C. and a solution of tert-butyl 4-(tosyloxymethyl)piperidine-1-carboxylate (10.4 g, 28 mmol, 1.1 eq) in DMF (50 mL) was slowly added at 0 C. and stirring was continued at 65-70 C. for 16 hr. After completion of the reaction (monitored by thin layer chromatography, 30% ethyl acetate in hexanes, Rf=0.5), the reaction was quenched by adding ice cubes and the mixture was extracted with tert-butyl methyl ether (2*200 mL). The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel 100-200 mesh, eluting with a 25-40% gradient of ethyl acetate in hexanes to afford tert-butyl 4-((5-bromo-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl)piperidine-1-carboxylate (9.0 g, 90%) as an off white solid. LCMS purity: 80%; (ES+): m/z 394.26 (M+H+).

Reference： [1]Patent: US2017/298060,2017,A1 .Location in patent: Paragraph 0090; 0091

44
[ 1215387-58-8 ]
5-bromo-1-(piperidin-4-ylmethyl)-1H-pyrrolo[2,3-c]pyridine hydrochloride [ No CAS ]

Reference： [1]Patent: US2017/298060,2017,A1

45
[ 1215387-58-8 ]
(4-((5-bromo-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl)piperidin-1-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Patent: US2017/298060,2017,A1

46
[ 1215387-58-8 ]
[ 76-02-8 ]
1-(5-bromo-1H-pyrrolo[2,3-c]pyridin-3-yl)-2,2,2-trichloroethanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10151 - 10171

47
[ 1215387-58-8 ]
5-(7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-N-methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10151 - 10171

48
[ 1215387-58-8 ]
methyl 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine-3-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10151 - 10171

49
[ 1215387-58-8 ]
methyl 5-(7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine-3-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10151 - 10171

50
[ 1215387-58-8 ]
5-bromo-1H-pyrrolo[2,3-c]pyridine-3-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10151 - 10171

51
[ 1215387-58-8 ]
5-(7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10151 - 10171

52
[ 1215387-58-8 ]
5-(7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-N-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10151 - 10171

53
[ 1187776-09-5 ]
[ 1215387-58-8 ]
4-(2-((5-bromo-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl)-1H-benzo[d]imidazol-1-yl)butan-1-ol [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 94 - 97

54
[ 557-21-1 ]
[ 1215387-58-8 ]
1H-pyrrolo[2,3-c]pyridine-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 147℃; for 3.5h;Microwave irradiation;	To a solution of 5-bromo-lH-pyrrolo[2,3-c]pyridine (0.9 g, 4.57 mmol, 1.0 eq), Zn(CN)2 (0.32 g, 2.74 mmol, 0.6 eq), Pd(PPh3)4 (234.5 mg, 0.457 mmol, 0.1 eq) in DMF (11.0 mL) at 147 C for 3.5 h under microwave irridiation. After the reaction was complete, it was extracted with EA. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (EA/PE = 1/1, v/v) to provide lH-pyrrolo[2,3-c]pyridine-5-carbonitrile (0.567 g, 78%).

Reference： [1]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00688

55
[ 1215387-58-8 ]
N-((6-amino-2,4-dimethylpyridin-3-yl)methyl)-1-((3-chloroquinolin-6-yl)methyl)-5-cyano-1H-pyrrolo[2,3-c]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

56
[ 1215387-58-8 ]
3-iodo-1H-pyrrolo[2,3-c]pyridine-5-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

57
[ 1215387-58-8 ]
1-((3-chloroquinolin-6-yl)methyl)-3-iodo-1H-pyrrolo[2,3-c]pyridine-5-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

58
[ 1215387-58-8 ]
methyl 1-((3-chloroquinolin-6-yl)methyl)-5-cyano-1H-pyrrolo[2,3-c]pyridine-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

59
[ 1215387-58-8 ]
1-((3-chloroquinolin-6-yl)methyl)-5-cyano-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

60
[ 1215387-58-8 ]
1-butyl-5-(trimethylstannyl)-1H-pyrrolo[2,3-c]pyridine [ No CAS ]