[ CAS No. 953039-63-9 ]

Name: 8-Bromo-2-chloro-6-fluoroquinazoline
Brand: Ambeed
SKU: A186965
Rating: 93 (30 reviews)

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Quality Control of [ 953039-63-9 ]

COA GC NMR CNMR HPLC/UPLC LC-MS

Related Doc. of [ 953039-63-9 ]

SDS

Product Details of [ 953039-63-9 ]

CAS No. :	953039-63-9	MDL No. :	MFCD18382554
Formula :	C₈H₃BrClFN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	261.48	Pubchem ID :	59199299
Synonyms :

Computed Properties of [ 953039-63-9 ]

TPSA :Topological Polar Surface Area	25.8	H-Bond Acceptor Count :	3
XLogP3 :	3.3	H-Bond Donor Count :	0
SP3 :	0.00	Rotatable Bond Count :	0

Safety of [ 953039-63-9 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 953039-63-9 ]

Upstream synthesis route of [ 953039-63-9 ]
Downstream synthetic route of [ 953039-63-9 ]

[ 953039-63-9 ] Synthesis Path-Upstream 1~4

1
[ 953039-62-8 ]
[ 953039-63-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	at 110℃; for 1.00 h;	Step 5. 8-Bromo-2-chloro-6-fluoroquinazolineA 0.5M suspension of 8-bromo-6-fluoroquinazolin-2-ol in phosphorus oxychloride was heated to 110 ⁰C in an oil bath. The suspension was turned to a brown color solution in 20min. LCMS data showed that the reaction was complete after 1 h. The phosphorus oxychloride was removed by concentration. The residue was mixed with ice water, and adjusted pH to 7 by adding sodium bicarbonate. Reaction mixture was extracted with ethyl acetate. Combined organic phase was washed with water, brine, dried over sodium sulfate and concentrated to give desired product in 89percent yield. ES/MS m/z 261/263 (MH⁺).

Reference： [1] Patent: WO2007/117607, 2007, A2. Location in patent: Page/Page column 332
[2] Patent: EP3287463, 2018, A1. Location in patent: Paragraph 0203; 0212
[3] Patent: US2018/208604, 2018, A1. Location in patent: Paragraph 0510-0511

2
[ 259269-84-6 ]
[ 953039-63-9 ]

Reference： [1] Patent: EP3287463, 2018, A1
[2] Patent: US2018/208604, 2018, A1
[3] Patent: WO2007/117607, 2007, A2

3
[ 55414-45-4 ]
[ 953039-63-9 ]

Reference： [1] Patent: EP3287463, 2018, A1
[2] Patent: US2018/208604, 2018, A1
[3] Patent: WO2007/117607, 2007, A2

4
[ 446-08-2 ]
[ 953039-63-9 ]

Reference： [1] Patent: EP3287463, 2018, A1
[2] Patent: US2018/208604, 2018, A1

[ 953039-63-9 ] Synthesis Path-Downstream 1~10

1
[ 953039-63-9 ]
[ 13061-96-6 ]
2-chloro-6-fluoro-8-methylquinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In N,N-dimethyl-formamide; at 120℃;	A mixture of <strong>[953039-63-9]8-bromo-2-chloro-6-fluoroquinazoline</strong> (500 mg, 1.91 mmol, 1 equiv), methylboronic acid (114.5 mg, 1.91 mmol, 1 equiv), K2CO3 (528.6 mg, 3.82 mmol, 2 equiv), Pd(dppf)Cl2 (139.9 mg, 0.19 mmol, 0.1 equiv) in 20 mL of DMF was stirred overnight at 120C. The reaction was then quenched by the addition of 50 mL of water, extracted with ethyl acetate (2x20 mL) and the combined organic layers concentrated. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1 :3) to afford the desired product as a yellow solid in 53% yield.
53%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In N,N-dimethyl-formamide; at 120℃;	A mixture of <strong>[953039-63-9]8-bromo-2-chloro-6-fluoroquinazoline</strong> (500 mg, 1.91 mmol, 1 equiv), methylboronic acid (114.5 mg, 1.91 mmol, 1 equiv), K2C03 (528.6 mg, 3.82 mmol, 2 equiv), Pd(dppf)Cl2 (139.9 mg, 0.19 mmol, 0.1 equiv) in 20 mL of DMF was stirred overnight at l20C. The reaction was then quenched by the addition of 50 mL of water, extracted with ethyl acetate (2x20 mL) and the combined organic layers concentrated. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1 :3) to afford the desired product as a yellow solid in 53% yield.

Reference： [1]Patent: WO2019/18562,2019,A1.Location in patent: Paragraph 0452
[2]Patent: WO2020/18848,2020,A1.Location in patent: Paragraph 0583

2
[ 953039-63-9 ]
4-(6-fluoro-8-(6-fluoro-pyridin-3-yl)-quinazolin-2-ylamino)benzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2007/117607,2007,A2

3
[ 953039-63-9 ]
C₂₈H₃₁FN₆O₃ [ No CAS ]

Reference： [1]Patent: US2018/208604,2018,A1

4
[ 953039-63-9 ]
6-fluoro-8-(2-methoxyphenyl)-N-[1-(4-piperidinyl)-1H-pyrazol-4-yl]quinazolin-2-amine [ No CAS ]

Reference： [1]Patent: US2018/208604,2018,A1

5
[ 446-08-2 ]
[ 953039-63-9 ]

Reference： [1]Patent: EP3287463,2018,A1
[2]Patent: US2018/208604,2018,A1

6
[ 953039-63-9 ]
C₃₁H₃₇FN₆O₃ [ No CAS ]