1261677-80-8|7-Bromoquinolin-5-ol| Ambeed

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Quality Control of [ 1261677-80-8 ] Purity: 98% SDS Specification

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Product Details of [ 1261677-80-8 ]

CAS No. :	1261677-80-8
Formula :	C₉H₆BrNO
M.W :	224.05
SMILES Code :	OC1=CC(Br)=CC2=C1C=CC=N2
MDL No. :	MFCD11878500
InChI Key :	DSLUBMAJPKDQJM-UHFFFAOYSA-N
Pubchem ID :	136216619

Safety of [ 1261677-80-8 ]

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

Application In Synthesis of [ 1261677-80-8 ]

* 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 [ 1261677-80-8 ]

[ 1261677-80-8 ] Synthesis Path-Downstream 1~13

1
[ 1261677-80-8 ]
[ 1421339-98-1 ]

References: [1]Patent: WO2013/14060,2013,A1 .
[2]Patent: US2013/29949,2013,A1 .

2
[ 1261677-80-8 ]
[ 1421340-06-8 ]

References: [1]Patent: WO2013/14060,2013,A1 .
[2]Patent: US2013/29949,2013,A1 .

3
[ 1261677-80-8 ]
[ 1421340-18-2 ]

References: [1]Patent: WO2013/14060,2013,A1 .
[2]Patent: US2013/29949,2013,A1 .

4
[ 1261677-80-8 ]
[ 1421341-28-7 ]

References: [1]Patent: WO2013/14060,2013,A1 .
[2]Patent: US2013/29949,2013,A1 .

5
[ 1261677-80-8 ]
[ 1421340-76-2 ]

References: [1]Patent: WO2013/14060,2013,A1 .
[2]Patent: US2013/29949,2013,A1 .

6
[ 16618-68-1 ]
[ 1261677-80-8 ]

References: [1]Patent: WO2013/14060,2013,A1 .
[2]Patent: US2013/29949,2013,A1 .

7
[ 1378860-76-4 ]
[ 1261677-80-8 ]

Yield	Reaction Conditions	Operation in experiment
41%		Step 2: 1.5 g (0.0064 mol) of 7-bromo-5-methoxy-quinoline were refluxed with 48% HBr (30 ml) for 20h. After cooling to room temperature reaction mixture was poured into 100 ml of water and basified with saturated ammonia solution. Product was filtered off, washed with water and dried at 50C in vacuo. Yield of 7-bromo-5-hydroxy-quinoline was 600 mg (41%>).1H-NMR (400 MHz, d6-DMSO): delta(lH,s), 7.48 (lH,m), 7.18 (lH,s) ppm.
41%	With hydrogen bromide; In water; for 20.0h;Reflux;	Step 2:[0123]1.5 g (0.0064 mol) of 7-bromo-5-methoxy-quinoline were refluxed with 48% HBr (30 ml) for 20 h. After cooling to room temperature reaction mixture was poured into 100 ml of water and basified with saturated ammonia solution. Product was filtered off, washed with water and dried at 50??? C. in vacuo. Yield of 7-bromo-5-hydroxy-quinoline was 600 mg (41%).[0124]1H-NMR (400 MHz, d6-DMSO): ????=11.1 (1H, s(broad)), 8.88 (1H, s), 8.49 (1H, d), 7.68 (1H,USD), 7.48 (1H, m), 7.18 (1H,USD) ppm.

References: [1]Patent: WO2013/14060,2013,A1 .Location in patent: Page/Page column 49.
[2]Patent: US2013/29949,2013,A1 .Location in patent: Paragraph 0122; 0123.

8
[ 1261677-80-8 ]
[ 1421339-96-9 ]

References: [1]Patent: WO2013/14060,2013,A1 .

9
[ 1261677-80-8 ]
[ 1421341-33-4 ]

References: [1]Patent: WO2013/14060,2013,A1 .

10
[ 1319738-37-8 ]
[ 1261677-80-8 ]
C₂₄H₂₅BrN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In dichloromethane; at 20℃;	A Example 27100 mg of 7-Bromo-quinolin-5-ol, 234 mg triphenylphosphine and 133 mg of (R)-4-((S)-l- hydroxyethyl)-l-((S)-l-(4-methoxyphenyl)ethyl)pyrrolidin-2-one was dissolved in 2.5 mL of DCM and 7.5 mL of THF. 205 mg DBAD was added (slightly exothermic) and the mixture was stirred overnight at room temperature. Then additional 234 mg triphenylphosphine and 205 mg DBAD was added and the mixture stirred over the weekend. The mixture was diluted with DCM and extracted with IN NaOH and water and the organic phase was concentrated in vacuo. The remaining material was treated with 2 mL of trifluoracetic acid (TFA) and heated 2 h and 15 min at 90C in the microwave. The mixture was concentrated and purified with HPLC (XbridgeC18, MeOH / water, TFA) to yield 165 mg yellow solid which was purified by FCC over silica ( 20 g Si02; DCM^ DCM: MeOH 90: 10) to yield 90 mg solid as Example 27. Analysis: HPLC-MS: Rt = 0.56 min (method X001 002), M+H = 335/337. 1H-NMR (400 MHz, DMSO-d6): delta = 8.95 (lH,d), 8.50 (lH,d), 7.80 (lH,s), 7.57 (2H, m), 7.30 (1H, s), 4.85 (1H, m), 3.40 (1H, t), 3.15-3.10 (1H, m), 2.82 (1H, m), 2.40-2.22 (2H,m), 1.32 (3H,d) ppm.

References: [1]Patent: WO2013/14060,2013,A1 .Location in patent: Page/Page column 87.

11
[ 1261677-80-8 ]
[ 115012-11-8 ]
[ 1421339-91-4 ]

Yield	Reaction Conditions	Operation in experiment
72 mg	With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; dichloromethane; at 20℃; for 14.0h;Inert atmosphere;	100 mg 7-Bromo-quinolin-5-ol, 77.5 mg of 2-(hydroxymethyl)nicotinamide 3.7, 233.5 mg of triphenylphosphine and 205 mg of Di-tertbutyl-azodicarboxylate (DBAD) were dissolved in 2.5 mL of DCM and 7.5 mL of THF under Argon at room temperature. After 14 h the precipitate was collected and dried. The mother liquor was concentrated and the formed precipitate again collected to yield 72 mg Example 22.Analysis: HPLC-MS: Rt = 0.48 min (method X001 002), M+H = 358/360.1H-NMR (400 MHz, DMSO-d6): delta = 8.91 (lH,d), 8.65 (lH,d), 8.48 (lH,d), 8.05 (1H, s), 7.95 (1H, d), 7.80 (1H, s), 6.65-7.50 (3H, m), 7.31 (lH,s), 5.58 (2H,s) ppm.
72 mg	With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; dichloromethane; at 20℃; for 14.0h;Inert atmosphere;	Synthesis of 2-((7-bromoquinolin-5-yloxy)methyl)nicotinamide (Example 22) 100 mg 7-Bromo-quinolin-5-ol, 77.5 mg of 2-(hydroxymethyl)nicotinamide 3.7, 233.5 mg of triphenylphosphine and 205 mg of Di-tertbutyl-azodicarboxylate (DBAD) were dissolved in 2.5 mL of DCM and 7.5 mL of THF under Argon at room temperature. After 14 h the precipitate was collected and dried. The mother liquor was concentrated and the formed precipitate again collected to yield 72 mg Example 22. Analysis: HPLC-MS: Rt=0.48 min (method X001-002), M+H=358/360. 1H-NMR (400 MHz, DMSO-d6): delta=8.91 (1H, d), 8.65 (1H, d), 8.48 (1H, d), 8.05 (1H, s), 7.95 (1H, d), 7.80 (1H, s), 6.65-7.50 (3H, m), 7.31 (1H,USD), 5.58 (2H,USD) ppm.

References: [1]Patent: WO2013/14060,2013,A1 .Location in patent: Page/Page column 78.
[2]Patent: US2013/29949,2013,A1 .Location in patent: Paragraph 0322; 0323; 0324; 0325.

12
[ 1261677-80-8 ]
[ 115012-11-8 ]
[ 1421339-93-6 ]

References: [1]Patent: WO2013/14060,2013,A1 .
[2]Patent: US2013/29949,2013,A1 .

13
[ 1319738-37-8 ]
[ 1261677-80-8 ]
[ 1421339-96-9 ]

Yield	Reaction Conditions	Operation in experiment
90 mg		Synthesis of (R)-4-((R)-1-(7-bromoquinolin-5-yloxy)ethyl)pyrrolidin-2-one (Example 27) 100 mg of 7-Bromo-quinolin-5-ol, 234 mg triphenylphosphine and 133 mg of (R)-4-((S)-1-hydroxyethyl)-1-((S)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one was dissolved in 2.5 mL of DCM and 7.5 mL of THF. 205 mg DBAD was added (slightly exothermic) and the mixture was stirred overnight at room temperature. Then additional 234 mg triphenylphosphine and 205 mg DBAD was added and the mixture stirred over the weekend. The mixture was diluted with DCM and extracted with 1N NaOH and water and the organic phase was concentrated in vacuo. The remaining material was treated with 2 mL of trifluoracetic acid (TFA) and heated 2 h and 15 min at 90 C. in the microwave. The mixture was concentrated and purified with HPLC (XbridgeC18, MeOH/water, TFA) to yield 165 mg yellow solid which was purified by FCC over silica (20 g SiO2; DCM?DCM:MeOH 90:10) to yield 90 mg solid as Example 27. Analysis: HPLC-MS: Rt=0.56 min (method X001-002), M+H=335/337. 1H-NMR (400 MHz, DMSO-d6): delta=8.95 (1H, d), 8.50 (1H, d), 7.80 (1H, s), 7.57 (2H, m), 7.30 (1H, s), 4.85 (1H, m), 3.40 (1H, t), 3.15-3.10 (1H, m), 2.82 (1H, m), 2.40-2.22 (2H, m), 1.32 (3H, d) ppm.

References: [1]Patent: US2013/29949,2013,A1 .Location in patent: Paragraph 0335; 0336; 0337; 0338.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Jones Oxidation • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Swern Oxidation

Related Functional Groups of
[ 1261677-80-8 ]

Bromides

A609492 [50488-36-3]

8-Bromo-6-methoxyquinoline

Similarity: 0.85

A275434 [82121-06-0]

7-Bromo-4-hydroxyquinoline

Similarity: 0.83

A174499 [13669-57-3]

3-Bromoquinolin-6-ol

Similarity: 0.83

A208160 [723283-89-4]

5-Bromoquinolin-4-ol

Similarity: 0.82

A602132 [103030-28-0]

6-Bromo-2-methylquinolin-4-ol

Similarity: 0.80

Alcohols

A275434 [82121-06-0]

7-Bromo-4-hydroxyquinoline

Similarity: 0.83

A174499 [13669-57-3]

3-Bromoquinolin-6-ol

Similarity: 0.83

A208160 [723283-89-4]

5-Bromoquinolin-4-ol

Similarity: 0.82

A122877 [23432-40-8]

6-Methylquinolin-4-ol

Similarity: 0.82

A602132 [103030-28-0]

6-Bromo-2-methylquinolin-4-ol

Similarity: 0.80

Related Parent Nucleus of
[ 1261677-80-8 ]

Quinolines

A609492 [50488-36-3]

8-Bromo-6-methoxyquinoline

Similarity: 0.85

A275434 [82121-06-0]

7-Bromo-4-hydroxyquinoline

Similarity: 0.83

A174499 [13669-57-3]

3-Bromoquinolin-6-ol

Similarity: 0.83

A208160 [723283-89-4]

5-Bromoquinolin-4-ol

Similarity: 0.82

A122877 [23432-40-8]

6-Methylquinolin-4-ol

Similarity: 0.82

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CAS No.: 1261677-80-8

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