[ CAS No. 1000340-39-5 ] {[proInfo.proName]}

Name: 1000340-39-5|3-Bromo-4-chloro-7-azaindole|96%
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SKU: A158827
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Quality Control of [ 1000340-39-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1000340-39-5 ]

CAS No. :	1000340-39-5	MDL No. :	MFCD09880132
Formula :	C₇H₄BrClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QLGXTRWCWHBPDP-UHFFFAOYSA-N
M.W :	231.48	Pubchem ID :	24729570
Synonyms :

Calculated chemistry of [ 1000340-39-5 ]

Physicochemical Properties

Num. heavy atoms :	11
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 :	48.8
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) :	-5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.74
Log Po/w (XLOGP3) :	2.63
Log Po/w (WLOGP) :	2.98
Log Po/w (MLOGP) :	2.32
Log Po/w (SILICOS-IT) :	3.35
Consensus Log Po/w :	2.6

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.54
Solubility :	0.0671 mg/ml ; 0.00029 mol/l
Class :	Soluble
Log S (Ali) :	-2.88
Solubility :	0.303 mg/ml ; 0.00131 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.39
Solubility :	0.00952 mg/ml ; 0.0000411 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 1000340-39-5 ]

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

Application In Synthesis of [ 1000340-39-5 ]

* 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 [ 1000340-39-5 ]
Downstream synthetic route of [ 1000340-39-5 ]

[ 1000340-39-5 ] Synthesis Path-Upstream 1~3

1
[ 55052-28-3 ]
[ 1000340-39-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃;	General procedure: 1H-4-chloro-pyrrolo[2,3-b]pyridine (0.763g, 5.0mmol, 1 eq.) was dissolved in DMF (7.5mL, 1.5mL/mmol SM) and NCS (0.701g, 5.25mmol, 1.05 eq.) was added. The resulting mixture was stirred at ambient temperature overnight, protected from light. Then, ice-cold water (25mL, 5mL/mmol SM) was added and the resulting precipitate filtered. The solids were washed four additional times with ice-cold water (4×10mL, 2mL/mmol SM). The solid was collected and dried under high vacuum to give 60 (0.861g, 4.6mmol) as an off-white solid in 92percent yield. Melting point: 236°C (decomposed). ¹H NMR (300MHz, DMSO‑d₆) δ: 7.21 (d, J=4.2Hz, 1H, H-5), 7.77 (s, 1H, H-2), 8.20 (d, J=4.2Hz, 1H, H-6), 12.35 (br. s, 1H, NH). ¹³C NMR (75MHz, DMSO‑d₆) δ: 101.1 (C-3), 113.7 (C-3a), 117.1 (C-5), 125.1 (C-2), 133.8 (C-4), 144.4 (C-6), 147.6 (7a). HRMS (ESI): calculated for C₇H₅Cl₂N₂ ([M+H]⁺): 186.9824, found: 186.9824.
90.9%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 6 h;	A 50ml of flask was charged with 1.52 g of 4-chloro-lH-pyrrolo[2,3-b]pyridine (prepared according to Tetrahedron Letters (2007), 48(9), 1527-1529), 2.7 gNBS and 29ml DMF. The mixture was stirred at rt for 6h. The solvent was evaporated off and purified by chromatography to give the 2.11 g of product, yield: 90.9percent.
58%	With N-Bromosuccinimide In acetone at 25℃; for 1 h;	Step 1 : A solution of C11 (9 g, 59.016 mM) in acetone (60 mL) was slowly added to a solution of N-N-bromosuccinimide (NBS) (10.44 g, 59.01 mM) in acetone (100 mL) at 25°C, and the reaction mixture was stirred for 1 hr. at 25⁰C. The solids were collected by filtration, washed with chilled acetone (5OmL), and dried under reduced pressure to provide 3-bromo-4- chloro-1 H-pyrrolo[2,3-b]pyridine (C38) as pale yellow solid. Yield: 7.5g, 58percent. ¹HNMR(CDCI₃) δ: 11.6-11.7 (b, 1 H), 8.1-8.2 (d, 1 H), 7.2-7.4 (s, 1 H), 7.0-7.01 (d, 1 H). Mass:(M+1) 231 calculated for mol. form. C₇H₄BrCIN₂.

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 248 - 267
[2] Patent: WO2008/5457, 2008, A2, . Location in patent: Page/Page column 180
[3] Patent: WO2008/12635, 2008, A2, . Location in patent: Page/Page column 90

2
[ 271-63-6 ]
[ 1000340-39-5 ]

Reference： [1] Patent: WO2008/5457, 2008, A2,

3
[ 1000340-39-5 ]
[ 68-12-2 ]
[ 918515-16-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; Stage #2: at -78 - 25℃; for 2 h;	Step 2: A solution of C38 (8 g, 34.632 mM) in THF (160 mL) was cooled to -78⁰C, treated with n-BuLi (1.6M, 5OmL, 79.63 mM), and stirred for 30 min. at -78⁰C. The cold solution was then slowly treated with DMF (5.056 g, 69.264m M). The reaction mixture was allowed to warm to 25°C, stirred for 2 hr., and treated with water (2 mL) to quench the reaction. The reaction mixture was concentrated under reduced pressure and treated with saturated aq. NH₄CI (28 mL), and the solids were collected and dried under reduced pressure. The resultant pale yellow solid (3.5g, 52percent) was then purified using silica gel column to provide 4-chloro-1 H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (C39). ¹HNMR(CDCI₃) 8: 12.6-12.8 (b,1 H),10.4-10.6 (s,1 H),8.26-8.3 (d,1 H),8.12-8.18 (s,1 H),7.26-7.3 (d,1 H). Mass:(M+1 ) 181 calculated for mol. form. C₈H₅CIN₂O.

Reference： [1] Patent: WO2008/12635, 2008, A2, . Location in patent: Page/Page column 90

[ 1000340-39-5 ] Synthesis Path-Downstream 1~28

1
[ 55052-28-3 ]
[ 1000340-39-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃;	General procedure: 1H-4-chloro-pyrrolo[2,3-b]pyridine (0.763g, 5.0mmol, 1 eq.) was dissolved in DMF (7.5mL, 1.5mL/mmol SM) and NCS (0.701g, 5.25mmol, 1.05 eq.) was added. The resulting mixture was stirred at ambient temperature overnight, protected from light. Then, ice-cold water (25mL, 5mL/mmol SM) was added and the resulting precipitate filtered. The solids were washed four additional times with ice-cold water (4×10mL, 2mL/mmol SM). The solid was collected and dried under high vacuum to give 60 (0.861g, 4.6mmol) as an off-white solid in 92% yield. Melting point: 236C (decomposed). 1H NMR (300MHz, DMSO-d6) delta: 7.21 (d, J=4.2Hz, 1H, H-5), 7.77 (s, 1H, H-2), 8.20 (d, J=4.2Hz, 1H, H-6), 12.35 (br. s, 1H, NH). 13C NMR (75MHz, DMSO-d6) delta: 101.1 (C-3), 113.7 (C-3a), 117.1 (C-5), 125.1 (C-2), 133.8 (C-4), 144.4 (C-6), 147.6 (7a). HRMS (ESI): calculated for C7H5Cl2N2 ([M+H]+): 186.9824, found: 186.9824.
96%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃;	1H-4-chloro-pyrrolo[2,3-b]pyridine (0.765 g, 5 mmol, 1 eq.) was dissolved in DMF (7.5 mL, 1 .5 mL / mmol SM). NBS (0.935 g, 5.25 mmol) was added and the resulting solution was stirred at ambient temperature overnight, protected from light. Then, the solution was poured into ice-cold water (25 mL, 5 mL / mmol SM) and cooled into an ice bath. After ~10min the remaining suspension was filtered and the solid washed four times with 10 mL ice-cold water. Then the solid was collected and dried under high vacuum to give FH5295 as a yellow solid (1 .12 g, 4.8 mmol) in 96 % yield. 1H NMR (300 MHz, DMSO-d6) delta: 7.23 (d, J = 5.1 Hz, 1 H, H-5), 7.81 (d, J = 2.7 Hz, 1 H, H-2), 8.21 (d, J = 5.1 Hz, 1 H, H-6), 12.44 (br s, 1 H, N-H). 13C NMR (75 MHz, DMSO-d6) delta: 85.03 (C-3), 1 14.58 (C-3a), 1 17.13 (C-5), 127.71 (C-2), 134.17 (C-4), 144.18 (C-6), 147.98 (C-7a). HRMS (ESI): calculated for C7H5BrCIN2 ([M+H]+): 230.9319, found: 230.9332. Melting point: 210 C (decomposed).
90.9%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 6h;	A 50ml of flask was charged with 1.52 g of 4-chloro-lH-pyrrolo[2,3-b]pyridine (prepared according to Tetrahedron Letters (2007), 48(9), 1527-1529), 2.7 gNBS and 29ml DMF. The mixture was stirred at rt for 6h. The solvent was evaporated off and purified by chromatography to give the 2.11 g of product, yield: 90.9%.

58%

With N-Bromosuccinimide; In acetone; at 25℃; for 1h;

Step 1 : A solution of C11 (9 g, 59.016 mM) in acetone (60 mL) was slowly added to a solution of N-N-bromosuccinimide (NBS) (10.44 g, 59.01 mM) in acetone (100 mL) at 25C, and the reaction mixture was stirred for 1 hr. at 250C. The solids were collected by filtration, washed with chilled acetone (5OmL), and dried under reduced pressure to provide 3-bromo-4- chloro-1 H-pyrrolo[2,3-b]pyridine (C38) as pale yellow solid. Yield: 7.5g, 58%. 1HNMR(CDCI3) delta: 11.6-11.7 (b, 1 H), 8.1-8.2 (d, 1 H), 7.2-7.4 (s, 1 H), 7.0-7.01 (d, 1 H). Mass:(M+1) 231 calculated for mol. form. C7H4BrCIN2.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 248 - 267
[2]Patent: WO2019/76633,2019,A1 .Location in patent: Page/Page column 36; 68; 106
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 8847 - 8865
[4]Patent: WO2008/5457,2008,A2 .Location in patent: Page/Page column 180
[5]Patent: WO2008/12635,2008,A2 .Location in patent: Page/Page column 90

2
[ 1000340-39-5 ]
[ 68-12-2 ]
[ 918515-16-9 ]

Yield	Reaction Conditions	Operation in experiment
52%		Step 2: A solution of C38 (8 g, 34.632 mM) in THF (160 mL) was cooled to -780C, treated with n-BuLi (1.6M, 5OmL, 79.63 mM), and stirred for 30 min. at -780C. The cold solution was then slowly treated with DMF (5.056 g, 69.264m M). The reaction mixture was allowed to warm to 25C, stirred for 2 hr., and treated with water (2 mL) to quench the reaction. The reaction mixture was concentrated under reduced pressure and treated with saturated aq. NH4CI (28 mL), and the solids were collected and dried under reduced pressure. The resultant pale yellow solid (3.5g, 52%) was then purified using silica gel column to provide 4-chloro-1 H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (C39). 1HNMR(CDCI3) 8: 12.6-12.8 (b,1 H),10.4-10.6 (s,1 H),8.26-8.3 (d,1 H),8.12-8.18 (s,1 H),7.26-7.3 (d,1 H). Mass:(M+1 ) 181 calculated for mol. form. C8H5CIN2O.

Reference： [1]Patent: WO2008/12635,2008,A2 .Location in patent: Page/Page column 90

3
[ 1000340-39-5 ]
[ 287944-16-5 ]
4-chloro-3-(3,6-dihydro-2H-pyran-4-yl)-1H-pyrrolo[ 2,3-b]pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091

4
[ 1000340-39-5 ]
4-chloro-3-(3,6-dihydro-2H-pyran-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091

5
[ 1000340-39-5 ]
3-(3,6-dihydro-2H-pyran-4-yl)-N-((1r,4r)-4-morpholinocyclohexyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091

6
[ 1000340-39-5 ]
N-((1r,4r)-4-morpholinocyclohexyl)-3-(tetrahydro-2hpyran-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091

7
[ 1000340-39-5 ]
N-((1r,4r)-4-morpholinocyclohexyl)-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091

8
[ 1000340-39-5 ]
[ 182825-17-8 ]
3-bromo-4-chloro-N1-(3′-C-ethynyl-2′,3′-5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		General procedure: In a flame-dried 2-neck round bottom flask, equipped with a stir bar was added the appropriate heterocycle (1.1 eq.) under argon. Then, anhydrous MeCN (7.5mL/mmol SM) was added, followed by BSA (1.2 eq.). The resulting suspension was stirred at ambient temperature for approximately 10min; after which a clear solution was obtained. Then, glycosyl donor, 18 [15] (1 eq.) was added in one portion, immediately followed by TMSOTf (1.25 eq.). The resulting solution was stirred at ambient temperature for another 15min, and then transferred to a pre-heated oil bath at 80C. Heating was continued until TLC analysis showed full consumption of the starting material (?2-3h), after which the mixture was cooled to ambient temperature. EA was added, and the mixture poured into a sat. aq. NaHCO3 solution. The layers were separated and the water layer extracted twice more with EA. The organic layers were combined, dried over Na2SO4, filtered and evaporated till dryness. The residue was purified by column chromatography 15% EA/Hexanes.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 248 - 267

9
[ 271-63-6 ]
[ 1000340-39-5 ]

Reference： [1]Patent: WO2008/5457,2008,A2

10
C₇H₈N₂O [ No CAS ]
[ 1000340-39-5 ]

Reference： [1]Patent: WO2008/5457,2008,A2

11
[ 10025-98-6 ]
[ 1000340-39-5 ]
C₁₄H₈Br₂Cl₄N₄Pd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; at 44.84℃; for 48h;	General procedure: K2PdCl4 and the seven halogeno-derivatives of 7-azaindole(3Cl7AIH, 3Br7AIH, 4Cl7AIH, 4Br7AIH, 5Br7AIH, 3Br4Cl7AIH and5Br3Cl7AIH) were purchased from Sigma-Aldrich.In the syntheses of trans-[PdCl2(L)2] we followed the procedure described earlier for obtaining trans-[PdCl2(7AIH)2] [24] and trans-[PdCl2(7AI3CAH)2] [25]. A hot aqueous solution (10 cm3) of K2PdCl4(0.5 mmol) was mixed with the ethanol solution of the appropriateligand (1.0 mmol, 20 cm3) and stirred at 318 K for 48 h. The obtained pale yellow solids were filtered off,washed with ethanol andthen dried. The results of the elemental analysis are collected in Table 1S in the Supplementary Data.

Reference： [1]Journal of Molecular Structure,2019,vol. 1181,p. 444 - 454

12
[ 10025-99-7 ]
[ 1000340-39-5 ]
cis-[PtCl₂(3-bromo-4-chloro-7-azaindole)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; at 44.84℃; for 48h;	General procedure: A hot aqueous solution (10 cm3) of K2PtCl4 (0.5 mmol) wasmixed with the ethanol solution of the appropriate ligand(1.0 mmol, 20 cm3) and stirred at 318 K for 48 h. The obtained paleyellow solids were filtered off, washed with ethanol and thendried. The results of the elemental analysis are collected inTable S1 in the Supplementary Data.

Reference： [1]Polyhedron,2019,vol. 173

13
[ 1000340-39-5 ]
3-bromo-4-amino-N1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 8847 - 8865

14
[ 6974-32-9 ]
[ 1000340-39-5 ]
3-bromo-4-chloro-N1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,3-b]pyridine [ No CAS ]