169674-02-6|4-Chloro-5-fluoro-1H-indole| Ambeed

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Quality Control of [ 169674-02-6 ] Purity: 97% SDS Specification

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Product Details of [ 169674-02-6 ]

CAS No. :	169674-02-6
Formula :	C₈H₅ClFN
M.W :	169.58
SMILES Code :	FC1=C(Cl)C2=C(NC=C2)C=C1
MDL No. :	MFCD12924664
InChI Key :	TUYZSKJQXNCPLN-UHFFFAOYSA-N
Pubchem ID :	11607987

Safety of [ 169674-02-6 ]

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

Application In Synthesis of [ 169674-02-6 ]

* 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 [ 169674-02-6 ]

[ 169674-02-6 ] Synthesis Path-Downstream 1~34

1
[ 169674-02-6 ]
[ 15448-47-2 ]
[ 169674-47-9 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2762 - 2769.

2
[ 169674-02-6 ]
[ 16088-62-3 ]
[ 169674-49-1 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2762 - 2769.

3
[ 908600-95-3 ]
[ 169674-02-6 ]

Yield	Reaction Conditions	Operation in experiment
80.1%	With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 0.5h;	A solution of tetrabutylammonium fluoride hydrate (1.9 g, 7.38 mmol) and compound 2 (1.2 g, 3.69 mmol) in THF (30 mL) was stirred for 30 min at room temperature. The mixture was diluted with diethyl ether (30 mL), washed with brine (30 mL), dried with sodium sulfate, filtered, and concentrated in vacuo. Purification by column chromatography (PE/EA=50:1) provided compound 3 (0.5 g, 80.1%) as a brown oil.

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.
[2]Patent: US2016/9706,2016,A1 .Location in patent: Paragraph 0354; 0357.

4
[ 908600-86-2 ]
[ 169674-02-6 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.
[2]Patent: US2016/9706,2016,A1 .

5
[ 908600-91-9 ]
[ 169674-02-6 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

6
[ 399-52-0 ]
[ 169674-02-6 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.
[2]Patent: US2016/9706,2016,A1 .

7
[ 1073-06-9 ]
[ 169674-02-6 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

8
[ 700-36-7 ]
[ 169674-02-6 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

9
[ 60144-53-8 ]
[ 169674-02-6 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

10
[ 371-40-4 ]
[ 169674-02-6 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

11
[ 408355-23-7 ]
[ 169674-02-6 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

12
[ 844891-31-2 ]
[ 169674-02-6 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

13
[ 169674-02-6 ]
(S)-2-(4-chloro-5-fluoro-indol-1-yl)-1-methyl-ethylamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2762 - 2769.

14
[ 169674-02-6 ]
(R)-2-(4-chloro-5-fluoro-indol-1-yl)-1-methyl-ethylamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2762 - 2769.

15
[ 169674-02-6 ]
[ 169674-48-0 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2762 - 2769.
[2]Patent: US5494928,1996,A .

16
[ 169674-02-6 ]
[ 169674-50-4 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2762 - 2769.
[2]Patent: US5494928,1996,A .

17
[ 169674-02-6 ]
Methanesulfonic acid (R)-2-(4-chloro-5-fluoro-indol-1-yl)-1-methyl-ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2762 - 2769.

18
[ 169674-02-6 ]
[ 1026919-15-2 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2762 - 2769.

19
ethyl acetate n-hexane [ No CAS ]
[ 914771-42-9 ]
[ 110-17-8 ]
[ 169674-02-6 ]
2-(4-chloro-5-fluoro-indol-1-yl)-ethylamine fumarate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; ammonia; ethylene dibromide;	d) A solution of 130 mg of <strong>[169674-02-6]4-chloro-5-fluoroindole</strong> in 3.7 ml of 1,2-dibromoethane was treated with 3.7 ml of 28% NaOH and 7.7 mg of tetrabutylammonium bromide. The mixture was stirred at 50 for 5 hours. The phases were separated and the aqueous phase was s extracted with toluene. The combined organic phases were washed with water and dried over sodium sulfate. The solvent was distilled off and the residue was chromatographed over 15 g of silica gel with hexane-ethyl acetate (5:1). There was obtained a yellow oil which was suspended in 30 ml of liquid ammonia and stirred in an autoclave at 80 for 16 hours. After evaporation of the ammonia the residue was taken up in dichloromethane and washed with water and saturated sodium chloride solution. The organic phase was dried over sodium sulfate and the solvent was distilled off. The residue was chromatographed over 15 g of silica gel with ethyl acetate-methanol (5:1). There were obtained 110 mg of a yellow oil which was dissolved in 16 ml of ether, treated with 60 mg (0.5 mmol) of fumaric acid and stirred for 2 days. The crystals were filtered off and dried. There were obtained 150 mg (59%) of 2-(4-chloro-5-fluoro-indol-1-yl)-ethylamine fumarate (1:1) with m.p. 200-201 (dec.)

References: [1]Patent: US5494928,1996,A .

20
4-chloro-5-fluoro-1H-indole-2-carboxylic acid [ No CAS ]
[ 169674-02-6 ]

Yield	Reaction Conditions	Operation in experiment
		c) A metal bath was heated to 300-320. 4.8 g of 4-chloro-5-fluoroindole-2-carboxylic acid were introduced under argon and, after three minutes, the metal bath was removed. The reaction mixture was distilled in a bulb-tube at 0.15 mbar and 75 bath temperature. There were obtained 3.15 g (83%) of 4-chloro-5-fluoroindole as white crystals with m.p. 41-43.

References: [1]Patent: US5494928,1996,A .

21
toluene-ethyl acetate [ No CAS ]
[ 169674-02-6 ]
[ 16088-62-3 ]
[ 169674-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; water;	a) A suspension of 0.11 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of <strong>[169674-02-6]4-chloro-5-fluoroindole</strong> at 0 and stirred at this temperature for 1 hour. After the addition of 0.4 ml of (S)-methyloxirane the reaction mixture was stirred at s room temperature for 48 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 30 g of silica gel with toluene-ethyl acetate (33:1). There was obtained 0.53 g (78.9%) of (S)-1-(4-chloro-5-fluoro-indol-1-yl)-propan-2-ol as a yellow oil.

References: [1]Patent: US5494928,1996,A .

22
toluene-ethyl acetate [ No CAS ]
[ 169674-02-6 ]
[ 15448-47-2 ]
[ 169674-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; water;	a) A suspension of 0.11 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of <strong>[169674-02-6]4-chloro-5-fluoroindole</strong> at 0 and stirred at this temperature for 1 hour. After the addition of 0.4 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 30 g of silica gel with toluene-ethyl acetate (33:1). There was obtained 0.5 g (74.5%) of (R)-1-(4-chloro-5-fluoro-indol-1-yl)-propan-2-ol as a yellow oil.

References: [1]Patent: US5494928,1996,A .

23
[ 169674-02-6 ]
[ 955978-88-8 ]

Yield	Reaction Conditions	Operation in experiment
		4-chloro-5-fluoro-1 H-pyrrolo[2,3-b]pyridine (500 mg, 2.931 mmol) in dioxane (12 ml.) was warmed to 40 C until a solution resulted. 4M HCI in dioxane solution (800 muIota_, 3.224 mmol) was added dropwise. The reaction mixture was cooled to room temperature and filtered. The solid was washed with diethyl ether and dried. It was then suspended in acetonitrile (10 ml.) and treated with sodium iodide (2.63 g, 17.55 mmol). The reaction mixture was heated at 80 C overnight. After cooling to room temperature, reaction mixture was treated with 1 N sodium hydroxide solution until it was basic. It was then extracted with ethyl acetate and washed with water. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried, filtered and concentrated under reduced pressure to afford 5-fluoro-4-iodo-1 H-indole.

References: [1]Patent: WO2015/187684,2015,A1 .Location in patent: Page/Page column 110.

24
[ 169674-02-6 ]
5-fluoro-4-iodo-1-(phenylsulfonyl)-1H-indole [ No CAS ]

References: [1]Patent: WO2015/187684,2015,A1 .

25
[ 169674-02-6 ]
5-(5-fluoro-1-(phenylsulfonyl)-1H-indol-4-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile [ No CAS ]

References: [1]Patent: WO2015/187684,2015,A1 .

26
[ 169674-02-6 ]
5-(5-fluoro-2-iodo-1-(phenylsulfonyl)-1H-indol-4-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile [ No CAS ]

References: [1]Patent: WO2015/187684,2015,A1 .

27
[ 68-12-2 ]
[ 169674-02-6 ]
C₉H₅ClFNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With trichlorophosphate; at 0 - 40℃; for 1.5h;	POCl3 (2.2 g, 14.5 mmol) was added dropwise to a solution of compound 3 (1.69 g, 10 mmol) in DMF (15 mL) at 0 C. The resulting mixture was stirred at 0 C. for 0.5 h, and additional DMF (5 mL) was added. The reaction mixture was stirred at 40 C. for 1 h. After it was cooled to rt, ice water (3 mL) was added and aqueous sodium hydroxide (4 M) was added to adjust pH to 11. The mixture was heated to reflux for 0.5 h. After it was cooled to rt, the mixture was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography (PE/EA=10:1) to provide the aldehyde (1.35 g, 69%) as a yellow solid.

References: [1]Patent: US2016/9706,2016,A1 .Location in patent: Paragraph 0354; 0358.

28
[ 169674-02-6 ]
4-chloro-5-fluoro-1H-indole-3-carboxylic acid [ No CAS ]

References: [1]Patent: US2016/9706,2016,A1 .

29
[ 169674-02-6 ]
C₉H₄Cl₂FNO [ No CAS ]

References: [1]Patent: US2016/9706,2016,A1 .

30
[ 169674-02-6 ]
C₁₇H₂₁BClFN₂O₂ [ No CAS ]

References: [1]Patent: US2016/9706,2016,A1 .

31
[ 169674-02-6 ]
quinuclidin-4-ylmethyl 4-chloro-5-fluoro-1H-indole-3-carboxylate hydrochloride [ No CAS ]

References: [1]Patent: US2016/9706,2016,A1 .

32
[ 153500-78-8 ]
[ 169674-02-6 ]

References: [1]Patent: US5494928,1996,A .

33
[ 169674-02-6 ]
(S)-2-(4-Chloro-5-fluoro-indol-1-yl)-1-methyl-ethylamine fumarate [ No CAS ]

References: [1]Patent: US5494928,1996,A .

34
[ 169674-02-6 ]
(R)-2-(4-Chloro-5-fluoro-indol-1-yl)-1-methyl-ethylamine fumarate [ No CAS ]

References: [1]Patent: US5494928,1996,A .

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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P321
P322
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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.: 169674-02-6

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