74420-05-6|N-Methyl-4-chloro-7-azaindole| Ambeed

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Quality Control of [ 74420-05-6 ] Purity: 96% SDS Specification

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Product Details of [ 74420-05-6 ]

CAS No. :	74420-05-6
Formula :	C₈H₇ClN₂
M.W :	166.61
SMILES Code :	C[N]2C1=NC=CC(=C1C=C2)Cl
MDL No. :	MFCD11501283
InChI Key :	GYGRXUOVLHHEMC-UHFFFAOYSA-N
Pubchem ID :	12646040

Safety of [ 74420-05-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 74420-05-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 74420-05-6 ]

[ 74420-05-6 ] Synthesis Path-Downstream 1~35

1
[ 55052-28-3 ]
[ 74-88-4 ]
[ 74420-05-6 ]

Yield	Reaction Conditions	Operation in experiment
96.33%		To a stirred solution of 4-chloro-lH-pyrrolo[2,3-b]pyridine (1.0 g, 6.554 mmol, 1.0 eq) in DMF (20 mL) was added NaH (60%) (0.53 g, 13.188 mmol, 2.0 eq) at 0C. The resulting mixture was allowed to stirred at the same temperature for 5 min followed by ad dition of CH3I (0.45 mL, 7.209 mmol, 1.1 eq). The resulting mixture was stirred at rt for 15 min. The progress of reaction was monitored by LCMS. The reaction mixture was poured into ice cold water (50 mL), extracted with EtOAc (2 x 50 mL), the combined organic layers were washed with water (50 mL), with brine (50 mL), dried over Na2S04, concentrated to afford the desired compound (1.05 g, 96.33%) as brown liquid. LCMS: (M+l)+l67.0
		General Procedure for Preparation of XYInt01; To a solution of azaindole derivative X in hexamethylphosphoramide (HMPA) at 0 C., natrium hydrogen (NaH; 1.2 eq) was added and stirred further. After 1 hour, an alkyl halides Y such as methyl iodide, ethyl iodide, n-propyl bromide, iso-propyl bromide, n-butyl bromide, isobutyl bromide (1.5 eq, 1 h) or O-t-butyldimethylsilyl-2-chloroethanol (10 eq, 24 h) or O-t-butyldimethylsilyl-2-chloropropanol (1.5 eq) was added and stirred. After completion of the reaction (monitored by thin layer chromatography (TLC)), the reaction was quenched by ice cold water and extracted with ethyl acetate (EtOAc; 3×). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to leave a residue of crude product. The crude product was purified by column chromatography to afford XYInt01 (75-85% yield).; Example 264; 4-chloro-N-(cycloheptylmethyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide; Synthesised according to the procedure disclosed in Example 2 where X is 4-chloro-7-azaindole, Y is methyl iodide, and Z is cycloheptylmethyl amine. Formula: C17H22ClN3O; Molecular Weight: 319.8; Mass/charge ratio: 319.1 (100.0%), 321.1 (32.4%), 320.1 (19.5%), 322.1 (6.3%), 321.2 (1.6%); Elemental analysis: C, 63.84; H, 6.93; Cl, 11.08; N, 13.14; O, 5.00.

References: [1]Patent: WO2020/12357,2020,A1 .Location in patent: Paragraph 000263.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1934 - 1937.
[3]Journal of Organic Chemistry,1980,vol. 45,p. 4045 - 4048.
[4]Patent: US2009/312366,2009,A1 .Location in patent: Page/Page column 12; 77.

2
[ 92-54-6 ]
[ 74420-05-6 ]
1-methyl-4-(4-phenyl-piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1934 - 1937.

3
[ 74420-05-6 ]
[ 64-04-0 ]
(1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-phenethyl-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1934 - 1937.

4
[ 74420-05-6 ]
[ 62-53-3 ]
N-phenyl-1-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1934 - 1937.

5
[ 74420-05-6 ]
[ 100-46-9 ]
N-benzyl-1-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1934 - 1937.

6
[ 271-63-6 ]
n-pentyl halide [ No CAS ]
[ 74420-05-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1934 - 1937.

7
[ 55052-24-9 ]
[ 74420-05-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1934 - 1937.

8
[ 74420-05-6 ]
[ 76-02-8 ]
C₁₀H₆Cl₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General Procedure for Preparation of XYInt02; To a solution of anhydrous AlCl3 (5 eq) in dry dimethylformamide (DMF) at 0 C. (20 mL) a solution of XYInt01 in dimethylformamide and the mixture was stirred further. After 1 hour, trichloroacetyl chloride (5 eq) was added and the mixture was allowed to warm to room temperature. After completion of the reaction (monitored by TLC), the reaction was quenched with ice-cold water and extracted with dimethylformamide (3×). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to leave a residue which was purified by column chromatography to afford XYInt02 (60-70% yield).; Example 264; 4-chloro-N-(cycloheptylmethyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide; Synthesised according to the procedure disclosed in Example 2 where X is <strong>[74420-05-6]4-chloro-7-azaindole</strong>, Y is methyl iodide, and Z is cycloheptylmethyl amine. Formula: C17H22ClN3O; Molecular Weight: 319.8; Mass/charge ratio: 319.1 (100.0%), 321.1 (32.4%), 320.1 (19.5%), 322.1 (6.3%), 321.2 (1.6%); Elemental analysis: C, 63.84; H, 6.93; Cl, 11.08; N, 13.14; O, 5.00.

References: [1]Patent: US2009/312366,2009,A1 .Location in patent: Page/Page column 12; 77.

9
[ 852292-27-4 ]
[ 74420-05-6 ]
[ 1431882-02-8 ]

References: [1]Chemical Communications,2013,vol. 49,p. 3970 - 3972.

10
[ 852292-27-4 ]
[ 74420-05-6 ]
[ 1431882-26-6 ]

References: [1]Chemical Communications,2013,vol. 49,p. 3970 - 3972.

11
[ 4248-19-5 ]
[ 74420-05-6 ]
[ 1374974-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 110℃; for 0.0833333h;Inert atmosphere;	To 100 mg B12.1 (commercially available, 0.60 mmol) was added 117 mg (1.5 eq) H2NBoc, 393 mg Cs2C03 (2 eq), 52 mg Xantphos (0.15 eq) and 27 mg Pd2(dba)3 (0.05 eq). To the above mixture was added degassed (Ar) dioxane. The suspension was further degassed for 5 minutes and then heated at 110C under an Ar atmosphere overnight. The reaction mixture was cooled and the dioxane was removed in vacuo. The residue was dissolved in DCM and then the DCM layer was washed with water. The DCM layer was concentrated to give crude B12.2. To crude B12.2 was added 4.0 M HCI in dioxane. The reaction mixture was stirred at room temperature for 3 hours and then the resulting solid was filtered, washed with Et20 and dried to give B12.3. To 264 mg (1.51 mmol) B5.1 in 2 mL DMF and 0.30 mL DIEA was added 2.5 mL of a ~1 mM stock solution of B51F in NMP. The reaction mixture was stirred for 15 minutes and then H20 was added. EtOAc utilized to extract product. Organic layer separated and then washed with 5% NaHC03,H20, and brine. EtOAc dried over MgS04 and concentrated. An Isco silica column (0 to 5% EtOAc in DCM) was run and product B12.4 was isolated (245 mg). To 100 mg B12.4 and B12.3 (89 mg) in 5 mL dioxane was added Cs2C03 (375 mg), rac-BINAP (52 mg), and Pd(OAc)2 (17 mg). The reaction mixture was degassed for 5 minutes and then heated at 90C for 1 hour and then at 110C for 30 minutes. The reaction was cooled and concentrated. DCM was added and the suspension was filtered. The filtrate was washed with H20 and was concentrated. An Isco silica column was run on the crude residue (0 to 7% MeOH in DCM) to afford pure B12.5. Nitrile to amide conversion (as detailed in Scheme 5) and Cbz-deprotection (as detailed in Scheme 7) afforded the title compound. MS found for C17H20F2N8O as (M+H)+391.2.

References: [1]Patent: WO2013/78468,2013,A1 .Location in patent: Paragraph 0544; 0545.

12
[ 74420-05-6 ]
[ 1374974-11-4 ]

References: [1]Patent: WO2013/78468,2013,A1 .

13
[ 74420-05-6 ]
C₂₅H₂₄F₂N₈O₂ [ No CAS ]

References: [1]Patent: WO2013/78468,2013,A1 .

14
[ 74420-05-6 ]
[ 73183-34-3 ]
C₁₄H₁₉BN₂O₂ [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 1408 - 1411.

15
[ 74420-05-6 ]
C₂₇H₂₁N₃O [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 1408 - 1411.

16
[ 74420-05-6 ]
1-methyl-4-(3-methylpyridin-2-yl)-7-aza-isatin [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 1408 - 1411.

17
[ 74420-05-6 ]
C₁₄H₁₃N₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 1408 - 1411.

18
[ 74420-05-6 ]
[ 292638-85-8 ]
(E)-methyl 3-(4-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acrylate [ No CAS ]

References: [1]Organic Letters,2016,vol. 18,p. 900 - 903.

19
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-4-methyl-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

20
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-4-methyl-6-oxo-1-(o-tolyl)-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

21
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-(3-fluorophenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

22
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-(4-fluorophenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

23
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-(3-bromophenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

24
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-(2-(trifluoromethyl)phenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

25
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-(3-(trifluoromethyl)phenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

26
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-(2,5-dimethylphenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

27
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-(2,4-dichlorophenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

28
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-(3-chloro-4-fluorophenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

29
[ 74420-05-6 ]
N-(4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-(4-bromo-2-fluorophenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

30
[ 74420-05-6 ]
N-(3-fluoro-4-((1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-(3-(trifluoromethyl)phenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

31
[ 74420-05-6 ]
4-((1-methyl-1H-pyrrolo [2,3-b]pyridin-4-yl)oxy)aniline [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.
[2]European Journal of Medicinal Chemistry,2018,vol. 143,p. 266 - 275.

32
[ 74420-05-6 ]
3-fluoro-4-((1-methyl-1H-pyrrolo [2,3-b]pyridin-4-yl)oxy)aniline [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.
[2]European Journal of Medicinal Chemistry,2018,vol. 143,p. 266 - 275.
[3]Bioorganic and medicinal chemistry letters,2019.

33
[ 100-02-7 ]
[ 74420-05-6 ]
4-((1-methyl-1H-pyrrolo [2,3-b]pyridin-4-yl)oxy)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In diphenylether; at 190℃; for 1h;	General procedure: 4-chloro-1H-pyrrolo[2,3-b]pyridine 9 (9.1g, 60mmol) or <strong>[74420-05-6]4-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridine</strong> 10 (10.0g, 60mmol) reacted with 4-nitrophenol 11a (12.5g, 90mmol) or 2-fluoro-4-nitrophenol 11b (14.1g, 90mmol) in diphenyl ether at 190C for 1h respectively. The mixture was cooled to 60C and poured into ethyl acetate (350mL) in an ice bath for 30-50min. The mixture was filtered off and dried to give light yellow solid 12a-d.

34
[ 402-67-5 ]
[ 74420-05-6 ]
C₁₄H₁₀FN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In diphenylether; at 190℃; for 1h;	General procedure: 4-chloro-1H-pyrrolo[2,3-b]pyridine 9 (9.1g, 60mmol) or <strong>[74420-05-6]4-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridine</strong> 10 (10.0g, 60mmol) reacted with 4-nitrophenol 11a (12.5g, 90mmol) or 2-fluoro-4-nitrophenol 11b (14.1g, 90mmol) in diphenyl ether at 190C for 1h respectively. The mixture was cooled to 60C and poured into ethyl acetate (350mL) in an ice bath for 30-50min. The mixture was filtered off and dried to give light yellow solid 12a-d.

References: [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 97 - 106.

35
[ 74420-05-6 ]
N-butyl-4-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide [ No CAS ]

References: [1]Chemical Communications,2017,vol. 53,p. 9446 - 9449.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
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
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
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
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
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

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CAS No.: 74420-05-6

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CAS No.: 74420-05-6

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[ 74420-05-6 ] Synthesis Path-Downstream 1~35

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