1227573-02-5|3-Bromo-5-fluoroisonicotinaldehyde| Ambeed

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Quality Control of [ 1227573-02-5 ] Purity: 98% SDS Specification

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Product Details of [ 1227573-02-5 ]

CAS No. :	1227573-02-5
Formula :	C₆H₃BrFNO
M.W :	204.00
SMILES Code :	O=CC1=C(F)C=NC=C1Br
MDL No. :	MFCD16606512
InChI Key :	ZGYWTNJGTMRSDK-UHFFFAOYSA-N
Pubchem ID :	53429192

Safety of [ 1227573-02-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 1227573-02-5 ]

* 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 [ 1227573-02-5 ]

[ 1227573-02-5 ] Synthesis Path-Downstream 1~21

1
[ 407-20-5 ]
[ 68-12-2 ]
[ 1227573-02-5 ]

Yield	Reaction Conditions	Operation in experiment
60.3%		Diisopropylamine (5.7 g, 28.4 mmol, 2.0 eq) was dissolved in anhydrous THF (200.0 mL), and the reaction mixture was cooled to -60 °C~ -65 °C, then n-ButLi (35.5 mL, 56.8 mmol, 2.0 eq) was added dropwise. The reaction mixture was stirred at the same temperature for 30.0 min, then 3-bromo-5-fluoropyridine (5.0 g, 28.4 mmol, 1.0 eq) in anhydrous THF (50.0 mL) was added to the reaction mixture at -60 °C~-65 °C and stirred at this temperature for 30 min. then DMF (2.5 g, 34.1 mmol, 1.2 eq) was added to the reaction mixture in one portion and stirred at this temperature for 30 min. The reaction was quenched by MeOH, then H4C1 solution was added, diluted by EA (200.0 mL), extracted by EA (200.0 mL X 3), washed by brine, concentrated. The resulting residue was purified by column chromatography (PE:EA = 3 : 1) to provide 3-bromo-5- fluoroisonicotinaldehyde (3.5 g, 60.3percent) as brown oil. LCMS (M+H+) m/z calculated 204.1, found 204.2.
22%		Step 1: 3-Bromo-5-fluoroisonicotinaldehyde To a LDA solution (1M in hexanes/THF, 12.55 mL, 12.55 mmol) was added a solution of 3-bromo-5-fluoropyridine (1.84 g, 10.46 mmol) in THF (20 ml) at -78° C. dropwise. The mixture was stirred at -78° C. for 1 h. Then DMF (1.62 mL, 1.53 g, 20.91 mmol) was added to the reaction mixture. After stirring at -78° C. for 30 min, the reaction mixture was quenched with aq. sat. NaHCO3 solution followed by extracting with EtOAC three times and DCM twice. All the organic layers were combined and dried over anhydrous Na2SO4. The solid was filtered out. Volatiles were removed under reduced pressure and the residue was purified with silica-gel chromatography (DCM) to afford the title compound (0.478 g, 22percent). 1H NMR (400 MHz, chloroform-d3) delta ppm=10.36 (s, 1H), 8.75 (s, 1H), 8.63-8.57 (m, 1H).
		n-Bu (16 M in hexanes, 2,250 mL, 3.60 mrnol) was added dropwise to a solution of dsisopropylamine (0.556 nil, 3,90 mmoi) in THF (20 ml) at -78 0C under innert gas (M2). The resulting mixture was warmed up to ~ -50 0C and stirred for 10 min and cooied again to -78 0C. A solution of 3-bromo-5-fluoropyridine (528 mg. 3 mmoi) in THF (5 ml) was added dropwise at this temperature. The reaction mixture turned from clear light brown to heterogenous light brown. After 30 min, DMF (0.256 ml, 3.30 mmoi) was added dropwise and the resulting mixture was stirred for 30 min. The reaction was quenched by MeOH then NH4C. (saturated solution) and warmed up to room temperature. After concentration, the residue was dissolved in CH2Ci2 and washed with NaHCOS (Saturated solution). After drying over Na2SO4, concentration, the residue was purified by column (Heptane to CH2CS2) and yielded sightiy yellow crystal (380 mg). 1H NMR (400,3 MHz, CDCb): 6 8.58 (s, 1H), 8.72 (s, 1H), 10.33 (s, 1 H),

Step 2: 3-Bromo-5-fluoro-pyridine-4-carbaldehyde (15b)n-BuLi (13.85 mL, 22.16 mmol) was added to a solution of diisopropylamine (3.16 mL, 22.16 mmol) in THF (50 mL) at -78 °C. After 30 min, 3-bromo-5-fluoropyridine (3.0 g, 17.05 mmol) in THF (25 mL) was added dropwise. The mixture was stirred for 1 hr, and then DMF (3.96 mL, 51.1 mmol) was added dropwise. Saturated aqueous NaHC03 was added and the cooling bath was removed. The mixture was shaken with ethyl acetate and the organic phase was washed with brine, dried over MgS04, and concentrated in vacuo. The residue was purified by silica gel flash chromatography employing dichloromethane-methanol, 9:1 to give 3-fluoro-5-(1 -oxo-1, 3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde. 1H NMR (400 MHz, DMSO-de) delta ppm 8.81 (d, J=1.4 Hz, 1 H), 8.83 (s, 1 H), 10.17 (s, 1 H)

References: [1]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00661.
[2]Patent: US2018/111932,2018,A1 .Location in patent: Paragraph 0406; 0407.
[3]Patent: WO2010/130773,2010,A2 .Location in patent: Page/Page column 77-78.
[4]Patent: WO2011/61168,2011,A1 .Location in patent: Page/Page column 61.

2
[ 1220696-32-1 ]
[ 1227573-02-5 ]
[ 1255713-83-7 ]

Yield	Reaction Conditions	Operation in experiment
35%		A mixture of 3-iVtelhyi-5-{4,4,5,5-tetraroethyi-(1 ,3,2]dioxabora.an-2-yl)-3H-benzalphaoxazoi-2- one (138 mg, 0,5 mmoi), 3-Bromo5~f1uoro~pyridine~4~carbafdehyde (102 mg, 0,5 mmoi), Na2CO3 (2 M in water, 0.75 mL, 1.5 mmoi) and PdCI2(PPh3)2 (17 mg, 0.03 mmoi) in DMF(3 mL) was heated at 1000C for 4 hrs. After concentration, the residue was diluted with DCM and saturated NH4C. solution. After filtration and concentration, the residue was purified by flash column (MeOH-C H2CI2, v/v, 0 - 1.5percent) and afforded the title compound (47 mg, 35percent). 1H NMR (400.3 MHz, CDCi3): S 3.45 (s, 3H), 6,96 (d, J = 1.7 Hz, 1H), 7.08 (dd, J = 8, 1.7 Hz, 1 H), 7.32 (d, J - 8 Hz, 1H), 8.59 (s, 1H), 8.68 (d, J - 1.3 Hz, I H), 10.07 (s, 1H),

References: [1]Patent: WO2010/130773,2010,A2 .Location in patent: Page/Page column 78.

3
[ 862081-37-6 ]
[ 1227573-02-5 ]
[ 1308670-19-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 100℃; for 1h;Inert atmosphere;	Step 2: 3-fluoro-5-(1-oxo-1 ,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde (35b) To 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-isobenzofuran-1-one (210 mg, 0.809 mmol) in DMF (4 mL) was added <strong>[1227573-02-5]3-bromo-5-fluoro-pyridine-4-carbaldehyde</strong> (150 mg, 0.735 mmol) and 2M aqueous sodium carbonate (0.735 mL, 1.471 mmol). The reaction mixture was flushed and evacuated with N2 twice followed by the addition of PdCI2(dppf).CH2CI2 adduct (30.0 mg, 0.037 mmol). The reaction mixture was stirred at 100 °C for 1 hour. The reaction was cooled to room temperature, diluted with ethyl acetate and washed with water twice. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to afford 3-fluoro-5-(1 -oxo-1 ,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde, which was taken into the next step without further purification.

References: [1]Patent: WO2011/61168,2011,A1 .Location in patent: Page/Page column 78-79.

4
[ 862081-37-6 ]
[ 1227573-02-5 ]
[ 1308669-44-4 ]

References: [1]Patent: WO2011/61168,2011,A1 .

5
[ 548797-51-9 ]
[ 1227573-02-5 ]
[ 1308669-84-2 ]

Yield	Reaction Conditions	Operation in experiment
18%	With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 100℃; for 4h;Inert atmosphere;	Step 3: 2-Chloro-4-(5-fluoro-4-formyl-pyridin-3-yl)-benzonitrile (15c)To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (264 mg, 1.00 mmol), <strong>[1227573-02-5]3-bromo-5-fluoroisonicotinaldehyde</strong> (204 mg, 1.00 mmol) and PdCI2(PPh3)2 (56 mg, 0.08 mmol) in DMF (3 mL) was added 2M Na2C03 solution (1.50 ml, 3.00 mmol) under nitrogen atmosphere. The mixture was stirred and heated at 100°C for 4hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and saturated NH4CI solution. After extraction and separation, the combined extracts were concentrated and purified by SNAPI Og (10percentMeOH/DCM 0- 15percentgradient) to give 2-chloro-4-(5-fluoro-4-formylpyridin-3-yl)benzonitrile (47 mg, 18percent) as a white solid.; ESI-MS m/z: 293 [M+MeOH+1]+, Retention time 1.15min. -NMR (CDCI3, 400 MHz) delta 7.33 (dd, J= 8.0, 1.6 Hz, 1 H), 7.50 (d, J= 1.6 Hz, 1 H), 7.78 (d, J= 8.0 Hz, 1 H), 8.49 (s, 1 H), 8.78 (d, J= 1.2 Hz, 1H), 10.27 (s, 1H)

References: [1]Patent: WO2011/61168,2011,A1 .Location in patent: Page/Page column 61.

6
[ 548797-51-9 ]
[ 1227573-02-5 ]
[ 1308668-85-0 ]

References: [1]Patent: WO2011/61168,2011,A1 .

7
[ 1227573-02-5 ]
[ 208934-35-4 ]
3-fluoro-5-[1-(triphenylmethyl)-1H-imidazol-4-yl]pyridine-4-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
610 mg	With Pd(amphos); In acetonitrile; at 100℃; for 4h;Inert atmosphere;	A mixture of <strong>[1227573-02-5]3-bromo-5-fluoropyridine-4-carbaldehyde</strong> (406 mg, 1.99 mmol), 4-(tributylstannyl)-1-(triphenylmethyl)-1H-imidazole (Intermediate A, 1.8 g, 3.0 mmol) and PdAMPHOS (142 mg, 0.20 mmol) in acetonitrile (12 mL) was stirred at 100° C. for 4 h under N2 atmosphere. Then the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (80 mL*2). The combined organic phase was washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with ethyl acetate in hexane (10percent to 30percent gradient) to yield 3-fluoro-5-[1-(triphenylmethyl)-1H-imidazol-4-yl]pyridine-4-carbaldehyde (610 mg, 71percent) as light yellow oil.

References: [1]Patent: US2016/75711,2016,A1 .Location in patent: Paragraph 0270-0271.

8
[ 1227573-02-5 ]
[ 208934-35-4 ]
1-cyclohexyl-3-[3-fluoro-5-[1-(triphenylmethyl)-1H-imidazol-4-yl]pyridin-4-yl]prop-2-en-1-one [ No CAS ]

References: [1]Patent: US2016/75711,2016,A1 .

9
[ 407-20-5 ]
[ 109-94-4 ]
[ 1227573-02-5 ]

Yield	Reaction Conditions	Operation in experiment
60%		n-BuLi (5.5 mL, 14 mmol) was added to a stirred solution of N,N-diisopropylamine (1.5 g, 15 mmol) in THF (50 mL) slowly at -78 °C. The temperature was allowed to reach -50 °C and stirred at this temperature for 30 minutes. The solution was cooled to -78 °C and to it was added a solution of 3-Bromo-5-fluoropyridine (2.09, 1.1 mmol) in THF (15 mL). The resulting mixture was stirred at this temperature for 45 minutes. A solution of ethyl formate (8.4 g, 113 mmol) in THF (15 mL) was added over 15 minutes and the resulting mixture was stirred at this temperature for 1 .5 hours. A saturated solution of NH4CI was added and the resulting mixture was partitioned with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel to afford a bright yellow solid characterised as 3-bromo-5-fluoro- pyridine-4-carbaldehyde (1.4 g, 60percent yield). 1H NMR (CDCI3, 400 MHz) O: 10.32 (5, 1H), 8.71 (5, 1H), 8.567 (5, 1H).

References: [1]Patent: WO2016/59412,2016,A1 .Location in patent: Page/Page column 00194; 00195.

10
[ 1227573-02-5 ]
N-((6-amino-2,4-dimethylpyridin-3-yl)methyl)-1-((3-chloroquinolin-6-yl)methyl)-4-cyano-1H-pyrazolo[3,4-c]pyridine-3-carboxamide [ No CAS ]