66490-20-8|6-Chlorobenzothiophene| Ambeed

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Quality Control of [ 66490-20-8 ] Purity: 98% SDS Specification

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Product Details of [ 66490-20-8 ]

CAS No. :	66490-20-8
Formula :	C₈H₅ClS
M.W :	168.64
SMILES Code :	ClC1=CC=C2C=CSC2=C1
MDL No. :	MFCD18451626
InChI Key :	APAMKXUATGRDBB-UHFFFAOYSA-N
Pubchem ID :	12398601

Safety of [ 66490-20-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 66490-20-8 ]

* 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.

Downstream synthetic route of [ 66490-20-8 ]

[ 66490-20-8 ] Synthesis Path-Downstream 1~35

1
[ 101495-15-2 ]
[ 66490-20-8 ]

References: [1]Journal of Organic Chemistry,1955,vol. 20,p. 1056,1060.

2
[ 5339-33-3 ]
[ 66490-20-8 ]

References: [1]Journal of Organic Chemistry,1955,vol. 20,p. 1056,1060.

3
[ 66490-20-8 ]
[ 79-35-6 ]
6-chloro-2-(2,2-dichloro-1-fluoroethenyl)benzothiophene [ No CAS ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 3311 - 3317.

4
[ 66490-20-8 ]
[ 79099-07-3 ]
[ 180160-66-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1903 - 1905.

5
[ 66490-20-8 ]
[ 190906-92-4 ]
[ 346591-88-6 ]

Yield	Reaction Conditions	Operation in experiment
36%		EXAMPLE 43 [0279] Preparation of (2S)-(-)-3-[(2R,4R)-4-(6-Chlorobenzo[b]thiophen-2-yl)-2-methylpiperidinyl]-1-(1H-indol-4-yl)oxy-2-propanol oxalate (A) and (2S)-(+)-3-[(2S,4S)-4-(6-Chlorobenzo[b]thiophen-2-yl)-2-methylpiperidinyl]-1-(1H-indol-4-yl)oxy-2-propanol oxalate (B). [CHEMMOL-00089] [0280] Preparation of N-t-Butoxycarbonyl-4-(6-chlorobenzo[b]thiophen-2-yl)-4-piperidinol. [CHEMMOL-00090] [0281] Scheme IA, Step A: A solution of <strong>[66490-20-8]6-chlorobenzo[b]thiophene</strong> (3.3424 g, 19.8 mmol, prepared in example 41) in dry THF (90 mL) at -78 C. was treated with 1.6 M n-BuLi in hexanes (12.5 mL, 20.0 mmol) for 1 h. To this was cannulated (N-t-butoxycarbonyl-2-methyl-4-piperidone (420152, 2.6672 g, 12.5 mmol) in THF (10 mL) and the reaction mixture was stirred at -78 C. for 3 h. The cold bath was removed and the reaction was quenched after 10 min with 100 mL of saturated aqueous NaHCO3 solution and the mixture was extracted with EtOAc (3×250 mL). The organic layers were washed with 100 mL of brine, combined, dried over MgSO4 and concentrated. Purification by PrepLC 500A (0-30% Et2O/hexanes) afforded unreacted <strong>[66490-20-8]6-chlorobenzo[b]thiophene</strong> (2.0047 g, 60%) N-t-butoxycarbonyl-4-(4-chlorobenzo[b]thiophen-2-yl)-2-methyl-4-piperidinol (0.2528 g, 3.3%, resulted from the 4-chloro contamination in the starting <strong>[66490-20-8]6-chlorobenzo[b]thiophene</strong>), unreacted piperidone (0.4184 g, 16%) and the intermediate title piperidinol (2.7510 g, 36%). Ion Spray MS 382.0 (M+H)+.

References: [1]Patent: US2004/6229,2004,A1 .Location in patent: Page/Page column 39-40.
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2393 - 2397.

6
[ 26018-73-5 ]
[ 66490-20-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl acetamide; at 200℃; for 1h;Microwave irradiation;	To a solution of 6-chlorobenzothiophene-2-carboxylic acid Xl-9b (1.00 g, 4.70 mmol) inDMA (5 ml) was added DBU (2.86 g, 18.8 mmol) and reaction mixture was heated in10 microwave at 200C for 1 h. Progress of the reaction was monitored by TLC. Aftercompletion, the reaction mixture was diluted with H20 (30 ml) and extracted with EtOAc(3 x 20 ml). The organic layer was separated, dried over anhydrous Na2S04 andconcentrated under vacuum to afford 6-chlorobenzothiophene Xl-9 (0.51 g) as an offwhitesolid.15 This compound was used as such for the next reaction without further purification.20Yield: 65%1H NMR (400 MHz, DMSO-d5) o 7.41 (dd, J=8.56, 1.71 Hz, 1 H) 7.47 (d, J=5.38 Hz, 1 H)7.80 (d, J=5.38 Hz, 1 H) 7.89 (d, J=8.80 Hz, 1 H) 8.17 (d, J=0.98 Hz, 1 H).
	With copper; In quinoline; at 182℃; for 2h;	[000924] Compound 242C (420 mg, 1.98 mmol) and copper powder (63 mg, 0.99 mmol) were suspended in quinoline (10 mL) and the resulting mixture was heated at 185 C for 2 h. After cooling down to room temperature, ethyl acetate (25 mL) was added and the suspension was filtered. The filtered cake was washed with ethyl acetate (5 mL x 2) and the combined organic layers were washed with aqueous HC1 solution (2 N, 10 mL x 2). After drying over anhydrous sodium sulfate, the solution was filtered and evaporated in vacuo to give a residue. The crude product was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to afford Compound 242D.

References: [1]Tetrahedron Letters,2004,vol. 45,p. 9645 - 9647.
[2]Patent: WO2018/122232,2018,A1 .Location in patent: Page/Page column 245; 246.
[3]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 000924.

7
[ 66490-20-8 ]
[ 128852-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	In 4-chlorobenzo<b>thiophene;	C. 6-Chloro-benzo[b]thiophene-2-sulfonyl chloride The title compound is prepared as described in EXAMPLE 8, Part A substituting the 4-chloro-benzo[b]-thiophene and 6-Chloro-benzo[b]-thiophene mixture for thianaphthalene. The crude product is purified by column chromatography eluding with hexanes to yield the title compound as well as 4-chlorobenzo[b]thiophene-2-sulfonyl chloride as white solids.

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.
[2]Patent: US6281227,2001,B1 .

8
[ 66490-20-8 ]
4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

9
[ 66490-20-8 ]
[ 259807-58-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

10
[ 66490-20-8 ]
1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

11
[ 66490-20-8 ]
1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]-4-[[5-(pyridin-2-yl)pyrimidin-2-yl]carbonyl]piperazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

12
[ 66490-20-8 ]
1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]-4-[[5-(pyridin-4-yl)pyrimidin-2-yl]carbonyl]piperazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

13
[ 66490-20-8 ]
1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]piperazine hydrochloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

14
[ 66490-20-8 ]
[ 180160-68-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1903 - 1905.

15
[ 66490-20-8 ]
4-(6-chloro-benzo[b]thiophen-2-yl)-piperidine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1903 - 1905.

16
[ 66490-20-8 ]
4-(6-chloro-benzo[b]thiophen-2-yl)-2-methyl-piperidine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2393 - 2397.

17
[ 66490-20-8 ]
1-[4-(6-chloro-benzo[b]thiophen-2-yl)-piperidin-1-yl]-3-(1H-indol-4-yloxy)-propan-2-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1903 - 1905.

18
[ 66490-20-8 ]
(2S)-(+)-3-[(2R,4S)-[4-(6-chlorobenzo[b]thiophen-2-yl)-2-methylpiperidinyl]]-1-(1H-Indol-4-yl)oxy-2-propanol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2393 - 2397.

19
[ 66490-20-8 ]
(2S)-3-[(2S,4R)-[4-(6-chlorobenzo[b]thiophen-2-yl)-2-methylpiperidinyl]]-1-(1H-indol-4-yl)oxy-2-propanol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2393 - 2397.

20
[ 66490-20-8 ]
1-[4-(6-chloro-benzo[b]thiophen-2-yl)-2-methyl-piperidin-1-yl]-3-(1H-indol-4-yloxy)-propan-2-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2393 - 2397.

21
[ 66490-20-8 ]
6-chloro-2-(2,2-dichloro-1-fluoroethenyl)benzothiophene 1,1-dioxide [ No CAS ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 3311 - 3317.

22
[ 19993-65-8 ]
[ 66490-20-8 ]

References: [1]Journal of Organic Chemistry,1955,vol. 20,p. 1056,1060.

23
[ 325704-20-9 ]
[ 66490-20-8 ]

References: [1]Journal of Organic Chemistry,1955,vol. 20,p. 1056,1060.

24
[ 205054-85-9 ]
[ 66490-20-8 ]
[ 66490-33-3 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphoric acid; In chlorobenzene; for 6h;Heating / reflux;	A solution containing polyphosphoric acid (8 g) and chlorobenzene (50 mL) is heated at reflux. A solution containing 1-chloro-3-(2,2-dimethoxyethylsulfanyl)benzene (2.7 g, 11.6 mmol) in chlorobenzene (5 mL) is added dropwise to the refluxing polyphosphoric acid solution. After 6 hours, the solution is cooled to ambient temperature. The solution is diluted with CH2Cl2 and washed with water and saturated NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with hexanes to yield the title compounds (2.4 g, 9.0 mmol) as a 1:1 isomeric mixture. 1H NMR (CDCl3, 300 MHz) δ7.88 (m, 1H), 7.75 (m, 2H), 7.42 (m, 2H). MS (EI): m/z 168, 170 (M+), Cl pattern

References: [1]Patent: US2004/102450,2004,A1 .Location in patent: Page/Page column 68.

25
[ 66490-20-8 ]
[ 234107-52-9 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; N,N-dimethyl-formamide; In tetrahydrofuran; at -78 - 20℃;	A. 6-Chlorobenzo[b]thiophene-2-carboxaldehyde. To a solution of <strong>[66490-20-8]6-chlorobenzo[b]thiophene</strong> (1.0 g, 5.93 mmol) in THF (60 ML) at -78 C. is added a 1.6 M solution of n-BuLi in THF (3.9 ML, 6.23 mmol).After 10 minutes, 0.5 ML of DMF is added.The solution is stirred for 0.5 hours, then allowed to warm to ambient temperature.The solution is poured into a solution of saturated NH4Cl. The solution is diluted with ether and the layers are separated.The organic layer is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated.The title compound is obtained as a white solid. MS (EI): m/z 196 (M+).

References: [1]Patent: US2004/102450,2004,A1 .Location in patent: Page/Page column 69.

26
[ 66490-20-8 ]
[ 66490-33-3 ]
[ 128852-00-6 ]
[ 128852-07-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 4-chloro-benzo[b]thiophene and <strong>[66490-20-8]6-chlorobenzo[b]thiophene</strong> (11.8 g, 88.1 mmol), in 400 mL of THF at -78 C. is added n-BuLi (55 mL of a 1.6M solution in hexanes, 88.1 mmol). After 15 minutes, the solution is added by cannula to a precooled (-78 C.) solution of SO2 (200 g) in 100 mL of THF. After addition, the solution is allowed to warm to ambient temperature. After 0.5 hour, the solution is concentrated. The residue is suspended in hexanes (400 mL) and is cooled to 0 C. To the solution is added SO2Cl2 (12.5 g, 92.5 mmol). After stirring for 15 minutes, the solution is concentrated. The residue is dissolved in EtOAc. The organic solution is washed with saturated NH4Cl (aq.), H2O and saturated NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated. The crude product is dissolved in CH2Cl2 and filtered through a plug of silica gel. The crude product is purified by column chromatography eluting with hexanes to yield the title compound as well as 4-chlorobenzo[b]thiophene-2-sulfonyl chloride as white solids. [1511] 4-Chlorobenzo[b]thiophene-2-sulfonyl chloride: 1H NMR (CDCl3, 300 MHz) δ8.32 (m, 1H), 7.81 (m, 1H), 7.53 (m, 2H). [1512] 6-Chlorobenzo[b]thiophene-2-sulfonyl chloride: 1H NMR (CDCl3, 300 MHz) δ8.11 (s, 1H), 7.88 (m, 2H), 7.50 (m, 1H)

References: [1]Patent: US2004/102450,2004,A1 .Location in patent: Page/Page column 68.

27
[ 180160-64-9 ]
[ 66490-20-8 ]
[ 66490-33-3 ]
[ 19742-92-8 ]

Yield	Reaction Conditions	Operation in experiment
51%; 40%	With PPA; Polyphosphoric acid (PPA); In chlorobenzene; for 3.75h;Heating / reflux;	Preparation of 4-Chlorobenzo[b]thiophene and 6-Chlorobenzo[b]thiophene. [CHEMMOL-00085] [0265] A mixture of 3-chlorobenzenethiol (9.9 g, 68.5 mmol), K2CO3 (11.35 g, 82.1 mmol), and bromoacetaldehyde diethyl acetal (8.1 mL, 68.5 mmol) in acetone (250 mL) was stirred at room temperature for 24 h. The base and the salt formed were removed by filtration with ethereal rinse. The filtrate and washings were combined, concentrated, taken up in 250 mL of Et2O, and washed with 200 mL each of 0.5 N KOH and brine. The aqueous layers were back-extracted with 2×250 mL of Et2O. Combined organic layers were dried over MgSO4, concentrated, and dried under vacuum. [0266] To a heated and vigorously stirred biphasic solution of polyphosphoric acid (PPA) (ca. 35 g) and chlorobenzene (350 mL) was added dropwise the crude acetal in 100 mL of chlorobenzene over 2.5 h period. After heating at reflux for 1.25 h, the mixture was stirred overnight while allowed to cool to room temperature. The organic layer was separated by decantation, concentrated, taken up in EtOAc (300 mL), and washed with 200 mL each of saturated aqueous NaHCO3 and brine. The PPA layer was dissolved in H2O (ca. 500 mL) and extracted with 3×300 mL of EtOAc which was washed with the saturated aqueous NaHCO3 and brine used above. Combined organic layers were dried over MgSO4, concentrated, and purified by PrepLC 500A with hexanes as eluent to yield 4-chlorobenzo[b]thiophene (4.269 g, 40%) and 6-chlorobenzo[b]thiophene (5.896 g, 51%) which was contaminated with 3-chlorobenzenedisulfide. FDMS 168(M)+

References: [1]Patent: US2004/6229,2004,A1 .Location in patent: Page/Page column 38.

28
[ 66490-20-8 ]
[ 200714-63-2 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 68 4-chloro- and 6-chloro-2-(4-hydroxy-1-methylpiperidin-4-yl)benzothiophene Beginning with 1.0 gm (5.95 mMol) of a 1:1 mixture of 4-chloro- and <strong>[66490-20-8]6-chlorobenzothiophene</strong>, 1.03 gm (61%) of the title compounds were recovered as a slightly colored solid by the procedure described in Example 67. MS(FD): m/e=281 (M+) EA: Calculated for: C14 H16 NOSCl: Theory: C, 59.67; H, 5.72; N, 4.97. Found: C, 59.86; H, 5.60; N, 4.97.
		EXAMPLE 68 4-chloro- and 6-chloro-2-(4-hydroxy-1-methylpiperidin-4-yl)benzothiophene Beginning with 1.0 gm (5.95 mMol) of a 1:1 mixture of 4-chloro- and <strong>[66490-20-8]6-chlorobenzothiophene</strong>, 1.03 gm (61%) of the title compounds were recovered as a slightly colored solid by the procedure described in Example 67. MS(FD): m/e=281 (M+) EA: Calculated for: C14H16NOSCl: Theory: C, 59.67; H, 5.72; N, 4.97. Found: C, 59.86; H, 5.60; N, 4.97.

References: [1]Patent: US5846982,1998,A .
[2]Patent: EP812826,1997,A1 .

29
[ 66490-20-8 ]
methyl 5-(6-chloro-2-methyl-1-benzothiophen-3-yl)-2-[(2S)-2-(hydroxymethyl)morpholin-4-yl]benzoate [ No CAS ]