[ CAS No. 1083181-26-3 ] {[proInfo.proName]}

Name: 1083181-26-3|3-Iodo-1H-pyrrolo[3,2-b]pyridine|98%
Brand: Ambeed
SKU: A123705
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Quality Control of [ 1083181-26-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1083181-26-3 ]

Product Details of [ 1083181-26-3 ]

CAS No. :	1083181-26-3	MDL No. :	MFCD11559019
Formula :	C₇H₅IN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZLVQSDNBINQPHB-UHFFFAOYSA-N
M.W :	244.03	Pubchem ID :	46856430
Synonyms :

Calculated chemistry of [ 1083181-26-3 ]

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 :	48.81
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) :	-6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.39
Log Po/w (XLOGP3) :	1.72
Log Po/w (WLOGP) :	2.17
Log Po/w (MLOGP) :	1.5
Log Po/w (SILICOS-IT) :	3.04
Consensus Log Po/w :	1.96

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.1
Solubility :	0.193 mg/ml ; 0.00079 mol/l
Class :	Soluble
Log S (Ali) :	-1.94
Solubility :	2.81 mg/ml ; 0.0115 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.87
Solubility :	0.0331 mg/ml ; 0.000136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.08

Safety of [ 1083181-26-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1083181-26-3 ]

* 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 [ 1083181-26-3 ]
Downstream synthetic route of [ 1083181-26-3 ]

[ 1083181-26-3 ] Synthesis Path-Upstream 1~1

1
[ 272-49-1 ]
[ 1083181-26-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-iodo-succinimide In tetrahydrofuran at 20℃;	To a solution of lH-pyrrolo[3,2-b]pyridine (1.94 g, 16.4 mmol) in THF (10 mL) is added N- iodosuccimide (4.06 g, 18.1 mmol). Preciptation occurs after a few minutes. The reaction is continued to stri at rt overnight. The preciptate is collected by filtration and is washed with a smalll amount of THF and heptane. The resultin white solid is dried in vacuo. The yeild of the reaction is 4.1 g (quantitative). 1H NMR (OMSO-d6, 300 MHz) δ 8.40 (s, 1H), 7.90-7.70 (m, 2H), 7.15 (d, 1H). LC 0.41 min; MS m/z 245 (M+l).
93.5%	With N-iodo-succinimide In tetrahydrofuran at 20℃;	To a solution of lH-pyrrolo[3,2-b]pyridine (3.0 g, 25.4 mmol, 1.0 eq) in THF (20 mL) was added NIS (6.3 g, 27.9 mmol, 1.1 eq). Precipitation occurred after a few minutes. The stirring was continued at rt overnight. The precipitate was collected by filtration and washed with a small amount of THF. The resulting solid was dried in vacuum to give 3- iodo-lH-pyrrolo[3,2-b]pyridine (5.8 g, 93.5percent).
9.18 g	With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1.08333 h; Inert atmosphere	To a mixture of 1H-pyrrolo[3,2-b]pyridine (Purchased from Combi Blocks Inc.), (5 g) and DMF (100 mL) stirred under nitrogen at room temperature was added potassium hydroxide (9.02 g) followed by iodine (12.89 g) and the resulting mixture was stirred at room temperature for 1 h 5 min., then poured onto a mixture of Na₂S₂O₅.5H₂O (4.25 g), water (635 mL), and 28-30percent ammonium hydroxide (43 mL). The resultant mixture was cooled in an ice bath for 20 min, and the precipitate thus produced was filtered and washed with ice water then dried under vacuum to give the title compound (9.18 g). LCMS: m/z 245.39 [M+H]⁺. ¹H NMR (400 MHz, DMSO-d₆) ppm 7.17 (dd, J=8.1, 4.5 Hz, 1H) 7.72-7.87 (m, 2H) 8.38 (d, J=4.4 Hz, 1H) 11.74 (br. s., 1H)

9.18 g

With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1.08333 h; Inert atmosphere

To a mixture of 1H-pyrrolo[3,2-b]pyridine (Purchased from Combi Blocks Inc.), (5 g) and DMF (100 mL) stirred under nitrogen at room temperature was added potassium hydroxide (9.02 g) followed by iodine (12.89 g) and the resulting mixture was stirred at room temperature for 1 h 5 min., then poured onto a mixture of Na₂S₂O₅.5H₂O (4.25 g), water (635 mL), and 28-30percent ammonium hydroxide (43 mL).
The resultant mixture was cooled in an ice bath for 20 min, and the precipitate thus produced was filtered and washed with ice water then dried under vacuum to give the title compound (9.18 g).
LCMS: m/z 245.39 [M+H]⁺.
¹H NMR (400 MHz, DMSO-d₆) ppm 7.17 (dd, J=8.1, 4.5 Hz, 1H) 7.72-7.87 (m, 2H) 8.38 (d, J=4.4 Hz, 1H) 11.74 (br. s., 1H)

Reference： [1] Patent: WO2011/78984, 2011, A1, . Location in patent: Page/Page column 72
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 24, p. 6935 - 6938
[3] Patent: WO2018/11628, 2018, A1, . Location in patent: Paragraph 00203
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 14, p. 5129 - 5136
[5] Patent: US2015/94328, 2015, A1, . Location in patent: Paragraph 0349; 0350-0352
[6] Patent: WO2015/49574, 2015, A1, . Location in patent: Page/Page column 38

[ 1083181-26-3 ] Synthesis Path-Downstream 1~26

1
[ 272-49-1 ]
[ 1083181-26-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-iodo-succinimide; In tetrahydrofuran; at 20℃;	To a solution of lH-pyrrolo[3,2-b]pyridine (1.94 g, 16.4 mmol) in THF (10 mL) is added N- iodosuccimide (4.06 g, 18.1 mmol). Preciptation occurs after a few minutes. The reaction is continued to stri at rt overnight. The preciptate is collected by filtration and is washed with a smalll amount of THF and heptane. The resultin white solid is dried in vacuo. The yeild of the reaction is 4.1 g (quantitative). 1H NMR (OMSO-d6, 300 MHz) delta 8.40 (s, 1H), 7.90-7.70 (m, 2H), 7.15 (d, 1H). LC 0.41 min; MS m/z 245 (M+l).
93.5%	With N-iodo-succinimide; In tetrahydrofuran; at 20℃;	To a solution of lH-pyrrolo[3,2-b]pyridine (3.0 g, 25.4 mmol, 1.0 eq) in THF (20 mL) was added NIS (6.3 g, 27.9 mmol, 1.1 eq). Precipitation occurred after a few minutes. The stirring was continued at rt overnight. The precipitate was collected by filtration and washed with a small amount of THF. The resulting solid was dried in vacuum to give 3- iodo-lH-pyrrolo[3,2-b]pyridine (5.8 g, 93.5%).
9.18 g	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 1.08333h;Inert atmosphere;	To a mixture of 1H-pyrrolo[3,2-b]pyridine (Purchased from Combi Blocks Inc.), (5 g) and DMF (100 mL) stirred under nitrogen at room temperature was added potassium hydroxide (9.02 g) followed by iodine (12.89 g) and the resulting mixture was stirred at room temperature for 1 h 5 min., then poured onto a mixture of Na2S2O5.5H2O (4.25 g), water (635 mL), and 28-30% ammonium hydroxide (43 mL). The resultant mixture was cooled in an ice bath for 20 min, and the precipitate thus produced was filtered and washed with ice water then dried under vacuum to give the title compound (9.18 g). LCMS: m/z 245.39 [M+H]+. 1H NMR (400 MHz, DMSO-d6) ppm 7.17 (dd, J=8.1, 4.5 Hz, 1H) 7.72-7.87 (m, 2H) 8.38 (d, J=4.4 Hz, 1H) 11.74 (br. s., 1H)

9.18 g

With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 1.08333h;Inert atmosphere;

To a mixture of 1H-pyrrolo[3,2-b]pyridine (Purchased from Combi Blocks Inc.), (5 g) and DMF (100 mL) stirred under nitrogen at room temperature was added potassium hydroxide (9.02 g) followed by iodine (12.89 g) and the resulting mixture was stirred at room temperature for 1 h 5 min., then poured onto a mixture of Na2S2O5.5H2O (4.25 g), water (635 mL), and 28-30% ammonium hydroxide (43 mL). The resultant mixture was cooled in an ice bath for 20 min, and the precipitate thus produced was filtered and washed with ice water then dried under vacuum to give the title compound (9.18 g). LCMS: m/z 245.39 [M+H]+. 1H NMR (400 MHz, DMSO-d6) ppm 7.17 (dd, J=8.1, 4.5 Hz, 1H) 7.72-7.87 (m, 2H) 8.38 (d, J=4.4 Hz, 1H) 11.74 (br. s., 1H)

Reference： [1]Patent: WO2011/78984,2011,A1 .Location in patent: Page/Page column 72
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6935 - 6938
[3]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00203
[4]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136
[5]Patent: US2015/94328,2015,A1 .Location in patent: Paragraph 0349; 0350-0352
[6]Patent: WO2015/49574,2015,A1 .Location in patent: Page/Page column 38

2
[ 1083181-26-3 ]
[ 2557-77-9 ]
[ 1204321-20-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6935 - 6938

3
[ 1083181-26-3 ]
[ 1316228-53-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136

4
[ 1083181-26-3 ]
C₁₇H₂₂N₂O₂Si [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136

5
[ 1083181-26-3 ]
C₁₄H₁₄N₂O₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136

6
[ 1083181-26-3 ]
[ 1316228-29-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136

7
[ 24424-99-5 ]
[ 1083181-26-3 ]
[ 1316228-21-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 3h;	Example 1143-((1H-Pyrrolo[3,2-b]pyridin-3-yl)ethynyl)-7,7-dimethyl-7,8-dihydroquinolin one[00316]To a mixture of 3-iodo-1 H-pyrrolo[3,2-b]pyridine (732 mg, 3.00 mmol), DMAP (37 mg, 0.30 mmol) and TEA (0.56 mL, 4.00 mmol) in THF (15 mL) Boc20 (785 mg, 3.60 mmol) is added. The reaction mixture is stirred at r.t. for 3 h and concentrated at reduced pressure. The obtained residue is purified by column chromatography (silica gel, DCM/EtOAc, 10: 1 ) to give ie/f-butyl 3-iodo-1 /-/-pyrrolo[3,2-b]pyridine-1 -carboxylate (980 mg, 95%) as white solid.[00317]According to General Procedure 2, 3-ethynyl-7,7-dimethyl-7,8-dihydroquinolin- 5(6H)-one (450 mg, 2.26 mmol) is reacted with ie/f-butyl 3-iodo-1 /-/-pyrrolo[3,2- b]pyridine-1 -carboxylate (772 mg, 2.24 mmol) in the presence of PdCl2(PPh3)2 (50 mg, 0.07 mmol), and TEA (1 mL) in acetonitrile (3 mL) at reflux for 3 h. The crude product is purified by column chromatography (silica gel, DCM/EtOAc, 1 :1 ) and crystallized from EtOAc/diethyl ether to give the intermediate product ie/f-butyl 3-((7,7-dimethyl-5-oxo- 5,6,7,8-tetrahydroquinolin-3-yl)ethynyl)-1 /-/-pyrrolo[3,2-b]pyridine-1 -carboxylate (615 mg, 66%) as yellowish solid.[00318]To a solution of the Boc-protected intermediate (390 mg, 0.94 mmol) in DCM (25 mL) TFA (5 mL) is added. The mixture is stirred at r.t. for 3 h and neutralized with aqueous solution of K2CO3. The organic layer is separated, and the aqueous layer is extracted with DCM (4x50 mL). The combined organic layers are dried over Na2SO4 and concentrated at reduced pressure. The obtained residue is crystallized from acetone, washed with water and diethyl ether and dried to provide the title compound (230 mg, 78%).1H NMR (De-DMSO), deltaEta, 1 .06 (s, 6H), 2.61 (s, 2H), 3.05 (s, 2H), 7.35 (dd, 1 H), 8.04 (d, 1 H), 8.21 (s, 2H), 8.51 (d, 1 H), 8.86 (s, 1 H), 12.1 1 (s, 1 H). LC/MS (M+H)+ = 316, 357
8.21 g	With dmap; In dichloromethane; at 20℃;Inert atmosphere;	To a mixture of <strong>[1083181-26-3]3-iodo-1H-pyrrolo[3,2-b]pyridine</strong> (Intermediate 1), (6 g), 4-Dimethylaminopyridine (0.390 g) and DCM (60.0 mL) stirred at room temperature under nitrogen was added dropwise a solution of di-t-butyldicarbonate (8.05 g) in DCM (60 mL) and the reaction was stirred overnight at rt, then concentrated under vacuum. The residue was purified by column chromatography (normal phase, 100 g, Biotage SNAP cartridge KP-Sil, 50 mL per min, gradient 0% to 30% EtOAc in n-hexane) to give the desired compound (8.21 g). LCMS: m/z 345.45 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.69 (s, 9H) 7.31 (dd, J=8.3, 4.8 Hz, 1H) 7.99 (s, 1H) 8.33-8.45 (m, 1H) 8.64 (dd, J=4.7, 1.2 Hz, 1H)
8.21 g	With dmap; In dichloromethane; at 20℃;Inert atmosphere;	To a mixture of <strong>[1083181-26-3]3-iodo-1H-pyrrolo[3,2-b]pyridine</strong> (Intermediate 1), (6 g), 4-Dimethylaminopyridine (0.390 g) and DCM (60.0 mL) stirred at room temperature under nitrogen was added dropwise a solution of di-t-butyldicarbonate (8.05 g) in DCM (60 mL) and the reaction was stirred overnight at rt, then concentrated under vacuum. The residue was purified by column chromatography (normal phase, 100 g, Biotage SNAP cartridge KP-Sil, 50 mL per min, gradient 0% to 30% EtOAc in n-hexane) to give the desired compound (8.21 g). LCMS: m/z 345.45 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.69 (s, 9H) 7.31 (dd, J=8.3, 4.8 Hz, 1H) 7.99 (s, 1H) 8.33-8.45 (m, 1H) 8.64 (dd, J=4.7, 1.2 Hz, 1H)

Reference： [1]Patent: WO2012/52451,2012,A1 .Location in patent: Page/Page column 112-113
[2]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136
[3]Patent: US2015/94328,2015,A1 .Location in patent: Paragraph 0349; 0353-0355
[4]Patent: WO2015/49574,2015,A1 .Location in patent: Page/Page column 38

8
[ 1083181-26-3 ]
1-(4-fluorobenzyl)-N-(1-(hydroxymethyl)cyclopentyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2015/94328,2015,A1

9
[ 1083181-26-3 ]
2-(4-(bromomethyl)-3-fluorophenyl)-6-methylpyridine hydrobromide [ No CAS ]
1-(2-fluoro-4-(6-methylpyridin-2-yl)benzyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
580 mg	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	To a mixture of <strong>[1083181-26-3]3-iodo-1H-pyrrolo[3,2-b]pyridine</strong> (Intermediate 1), (350 mg) and potassium carbonate (791 mg) in DMF (8 mL) stirred at 0 C. under nitrogen was added 2-(4-(bromomethyl)-3-fluorophenyl)-6-methylpyridine hydrobromide (Intermediate 65), (620 mg). The reaction mixture was allowed to warm to rt and was stirred overnight. Water (50 mL) was added to the reaction mixture and the reaction mixture was extracted with EtOAc (100 mL). The organic phase was washed with brine (75 mL), dried (Na2SO4), filtered and evaporated under vacuum. The crude product was purified by column chromatography (silica) eluting with 28:72 EtOAc:hexanes to afford the title compound (580 mg) which was taken on as such. LCMS: m/z 444.11 [M+H]+.
580 mg	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	To a mixture of <strong>[1083181-26-3]3-iodo-1H-pyrrolo[3,2-b]pyridine</strong> (Intermediate 1), (350 mg) and potassium carbonate (791 mg) in DMF (8 mL) stirred at 0 C. under nitrogen was added 2-(4-(bromomethyl)-3-fluorophenyl)-6-methylpyridine hydrobromide (Intermediate 65), (620 mg). The reaction mixture was allowed to warm to rt and was stirred overnight. Water (50 mL) was added to the reaction mixture and the reaction mixture was extracted with EtOAc (100 mL). The organic phase was washed with brine (75 mL), dried (Na2SO4), filtered and evaporated under vacuum. The crude product was purified by column chromatography (silica) eluting with 28:72 EtOAc:hexanes to afford the title compound (580 mg) which was taken on as such. LCMS: m/z 444.11 [M+H]+.

Reference： [1]Patent: US2015/94328,2015,A1 .Location in patent: Paragraph 0524; 0531; 0532
[2]Patent: WO2015/49574,2015,A1 .Location in patent: Page/Page column 63; 64

10
[ 1083181-26-3 ]
4-(4-(bromomethyl)-3-fluorophenyl)-2-methylpyridine hydrobromide [ No CAS ]
1-(2-fluoro-4-(2-methylpyridin-4-yl)benzyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
480 mg	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	To a mixture of <strong>[1083181-26-3]3-iodo-1H-pyrrolo[3,2-b]pyridine</strong> (Intermediate 1), (300 mg) and potassium carbonate (678 mg) in DMF (5 mL) stirred at 0 C. under nitrogen was added 4-(4-(bromomethyl)-3-fluorophenyl)-2-methylpyridine hydrobromide (Intermediate 68), (531 mg). The reaction mixture was allowed to warm to rt and was stirred overnight. Water (35 mL) was added to the reaction mixture and the reaction mixture was extracted with EtOAc (2*35 mL). The organic phases were combined, washed with brine (40 mL), dried (Na2SO4), filtered and evaporated under vacuum. The crude product was purified by column chromatography (silica) eluting with 80:20 EtOAc:hexanes to afford the title compound (480 mg). LCMS: m/z 444.16 [M+H]+.
480 mg	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	To a mixture of <strong>[1083181-26-3]3-iodo-1H-pyrrolo[3,2-b]pyridine</strong> (Intermediate 1), (300 mg) and potassium carbonate (678 mg) in DMF (5 mL) stirred at 0 C. under nitrogen was added 4-(4-(bromomethyl)-3-fluorophenyl)-2-methylpyridine hydrobromide (Intermediate 68), (531 mg). The reaction mixture was allowed to warm to rt and was stirred overnight. Water (35 mL) was added to the reaction mixture and the reaction mixture was extracted with EtOAc (2*35 mL). The organic phases were combined, washed with brine (40 mL), dried (Na2SO4), filtered and evaporated under vacuum. The crude product was purified by column chromatography (silica) eluting with 80:20 EtOAc:hexanes to afford the title compound (480 mg). LCMS: m/z 444.16 [M+H]+.

Reference： [1]Patent: US2015/94328,2015,A1 .Location in patent: Paragraph 0533; 0541; 0542
[2]Patent: WO2015/49574,2015,A1 .Location in patent: Page/Page column 64; 65; 66

11
[ 1083181-26-3 ]
[ 459-46-1 ]
1-(4-fluorobenzyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
649 mg		To an ice-cold solution of <strong>[1083181-26-3]3-iodo-1H-pyrrolo[3,2-b]pyridine</strong> (Intermediate 1), (500 mg) in N,N-dimethylacetamide (5 mL) stirred at rt under nitrogen was added sodium hydride (98 mg) portionwise and the reaction was stirred for 10 min. 1-(Bromomethyl)-4-fluorobenzene (0.26 mL) in DMA (5 mL) was added dropwise and the reaction was stirred at rt overnight, at which point LC-MS indicated presence of the desired product. The reaction was diluted with EtOAc, washed with water (2), brine (2), dried (MgSO4), filtered and evaporated under vacuum. The residue was purified by column chromatography (normal phase, 25 g, Biotage SNAP cartridge KP-Sil, 25 mL per min, gradient 0% to 50% EtOAc in n-hexane) to yield the desired product (649 mg). LCMS: m/z 353.39 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 5.31 (s, 2H) 6.98-7.20 (m, 5H) 7.45 (s, 1H) 7.54 (d, J=8.2 Hz, 1H) 8.59 (d, J=4.5 Hz, 1H)
649 mg		To an ice-cold solution of <strong>[1083181-26-3]3-iodo-1H-pyrrolo[3,2-b]pyridine</strong> (Intermediate 1), (500 mg) in N,N-dimethylacetamide (5 mL) stirred at rt under nitrogen was added sodium hydride (98 mg) portionwise and the reaction was stirred for 10 min. 1-(Bromomethyl)-4-fluorobenzene (0.26 mL) in DMA (5 mL) was added dropwise and the reaction was stirred at rt overnight, at which point LC-MS indicated presence of the desired product. The reaction was diluted with EtOAc, washed with water (2), brine (2), dried (MgSO4), filtered and evaporated under vacuum. The residue was purified by column chromatography (normal phase, 25 g, Biotage SNAP cartridge KP-Sil, 25 mL per min, gradient 0% to 50% EtOAc in n-hexane) to yield the desired product (649 mg). LCMS: m/z 353.39 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 5.31 (s, 2H) 6.98-7.20 (m, 5H) 7.45 (s, 1H) 7.54 (d, J=8.2 Hz, 1H) 8.59 (d, J=4.5 Hz, 1H)

Reference： [1]Patent: US2015/94328,2015,A1 .Location in patent: Paragraph 0398-0401
[2]Patent: WO2015/49574,2015,A1 .Location in patent: Page/Page column 45

12
[ 1083181-26-3 ]
1-(4-fluorobenzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2015/94328,2015,A1
[2]Patent: WO2015/49574,2015,A1

13
[ 1083181-26-3 ]
1-(4-fluorobenzyl)-N-(trans-3-methyltetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2015/94328,2015,A1

14
[ 1083181-26-3 ]
1-(4-fluorobenzyl)-N-(trans-2-methylcyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2015/94328,2015,A1

15
[ 1083181-26-3 ]
N-(trans-4,4-difluoro-2-hydroxycyclohexyl)-1-(4-fluorobenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]
N-(trans-4,4-difluoro-2-hydroxycyclohexyl)-1-(4-fluorobenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/49574,2015,A1

16
[ 1083181-26-3 ]
2-(4-(bromomethyl)-3-fluorophenyl)-6-methylpyridine hydrobromide [ No CAS ]
1-(2-fluoro-4-(6-methylpyridin-2-yl)benzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2015/94328,2015,A1
[2]Patent: WO2015/49574,2015,A1

17
[ 1083181-26-3 ]
4-(4-(bromomethyl)-3-fluorophenyl)-2-methylpyridine hydrobromide [ No CAS ]
1-(2-fluoro-4-(2-methylpyridin-4-yl)benzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2015/94328,2015,A1
[2]Patent: WO2015/49574,2015,A1

18
[ 1083181-26-3 ]
[ 147497-57-2 ]
1-((4'-fluoro-[1,1'-biphenyl]-4-yl)methyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
700 mg		Sodium hydride (140 mg, 60% dispersion in mineral oil) was added to a solution of <strong>[1083181-26-3]3-iodo-1H-pyrrolo[3,2-b]pyridine</strong> (Intermediate 1), (700 mg) in dimethyl acetamide (7 mL) at 0 C. The RM was allowed to warm to rt and was stirred for 30 min. To which, was added 4-fluoro-4'-methyl-1,1'-biphenyl (Intermediate 71), (840 mg) and the reaction mixture stirred for a further 1 h. The reaction was quenched with water (20 mL) and extracted with EtOAc (3*20 mL). The organic phases were combined, dried (Na2SO4), filtered, and evaporated under vacuum. The crude product was purified by column chromatography (silica), eluting with 20:80 EtOAc/hexanes to afford the title compound (700 mg). LCMS: m/z 429.04 [M+H]+. 1H NMR (400 MHz, DMSO-d6) ppm 5.51 (s, 2H), 7.21 (dd, J=8.2, 4.6 Hz, 1H), 7.23-7.30 (m, 2H), 7.35 (d, J=8.2 Hz, 2H), 7.54-7.62 (m, 2H), 7.62-7.69 (m, 2H), 8.00 (dd, J=8.2, 1.2 Hz, 1H), 8.09 (s, 1H), 8.40 (dd, J=4.4, 1.4 Hz, 1H)
700 mg		Sodium hydride (140 mg, 60% dispersion in mineral oil) was added to a solution of <strong>[1083181-26-3]3-iodo-1H-pyrrolo[3,2-b]pyridine</strong> (Intermediate 1), (700 mg) in dimethyl acetamide (7 mL) at 0 C. The RM was allowed to warm to rt and was stirred for 30 min. To which, was added 4-fluoro-4'-methyl-1,1'-biphenyl (Intermediate 71), (840 mg) and the reaction mixture stirred for a further 1 h. The reaction was quenched with water (20 mL) and extracted with EtOAc (3*20 mL). The organic phases were combined, dried (Na2SO4), filtered, and evaporated under vacuum. The crude product was purified by column chromatography (silica), eluting with 20:80 EtOAc/hexanes to afford the title compound (700 mg). LCMS: m/z 429.04 [M+H]+. 1H NMR (400 MHz, DMSO-d6) ppm 5.51 (s, 2H), 7.21 (dd, J=8.2, 4.6 Hz, 1H), 7.23-7.30 (m, 2H), 7.35 (d, J=8.2 Hz, 2H), 7.54-7.62 (m, 2H), 7.62-7.69 (m, 2H), 8.00 (dd, J=8.2, 1.2 Hz, 1H), 8.09 (s, 1H), 8.40 (dd, J=4.4, 1.4 Hz, 1H)

Reference： [1]Patent: US2015/94328,2015,A1 .Location in patent: Paragraph 0543; 0547-0549
[2]Patent: WO2015/49574,2015,A1 .Location in patent: Page/Page column 66; 67

19
[ 1083181-26-3 ]
[ 147497-57-2 ]
1-((4'-fluoro-[1,1'-biphenyl]-4-yl)methyl)-N-(trans-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2015/94328,2015,A1
[2]Patent: WO2015/49574,2015,A1

20
[ 1083181-26-3 ]
tert-butyl 3-((trans-3-hydroxytetrahydro-2H-pyran-4-yl)carbamoyl)-1H-pyrrolo[3,2-b]pyridine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2015/94328,2015,A1
[2]Patent: WO2015/49574,2015,A1

21
[ 1083181-26-3 ]
N-(cis-4,4-difluoro-2-hydroxycyclohexyl)-1-(4-fluorobenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2015/94328,2015,A1

22
[ 1083181-26-3 ]
N-(trans-4,4-difluoro-2-hydroxycyclohexyl)-1-(4-fluorobenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2015/94328,2015,A1

23
[ 1083181-26-3 ]
3-chloro-6-(chloromethyl)quinoline [ No CAS ]
3-chloro-6-(3-iodopyrrolo[3,2-b]pyridin-1-ylmethyl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	A mixture of 3-iodo-lH-pyrrolo[3,2-b]pyridine (2.1 g, 10 mmol, 1 eq), 3-chloro- 6-chloromethyl-quinoline (2.9 g, 12 mmol, 1.2 eq) and K2C03 (2.8 g, 20 mmol, 2 eq) in DMF (60 mL) was stirred at rt overnight and then concentrated. The residue was washed with water, and the resulting precipitate was collected by filtration to give 3-chloro-6-(3- iodo-pyrrolo[3,2-b]pyridin-l-ylmethyl)-quinoline (2.9 g, 69%).

Reference： [1]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00204

24
[ 1083181-26-3 ]
1-(3-chloroquinolin-6-ylmethyl)-1H-pyrrolo[3,2-b]pyridine-3-carbonitrile [ No CAS ]

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

25
[ 1083181-26-3 ]
1-(3-chloroquinolin-6-ylmethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid [ No CAS ]

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

26
[ 1083181-26-3 ]
N-((6-amino-2,4-dimethylpyridin-3-yl)methyl)-1-((3-chloroquinolin-6-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide [ No CAS ]

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

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Code	Phrase
H300	Fatal if swallowed
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H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
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H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
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H370	Causes damage to organs
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H372	Causes damage to organs through prolonged or repeated exposure
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
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. 1083181-26-3 ] {[proInfo.proName]}

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[ 1083181-26-3 ] Synthesis Path-Upstream 1~1

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