[ CAS No. 153034-82-3 ]

Name: 153034-82-3|2-Fluoro-4-iodonicotinaldehyde|97%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 153034-82-3 ]

CAS No. :	153034-82-3	MDL No. :	MFCD03095290
Formula :	C₆H₃FINO	Boiling Point :	304.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	251.00 g/mol	Pubchem ID :	9992328
Synonyms :

Safety of [ 153034-82-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 153034-82-3 ]

Upstream synthesis route of [ 153034-82-3 ]
Downstream synthetic route of [ 153034-82-3 ]

[ 153034-82-3 ] Synthesis Path-Upstream 1~6

1
[ 113975-22-7 ]
[ 109-94-4 ]
[ 153034-82-3 ]

Yield	Reaction Conditions	Operation in experiment
46%	Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -70℃; for 2 h; Stage #2: at -70 - 20℃;	To a solution of diisopropylamine (174.4g, 1 .73 mol) in dry THF (3 L) was added dropwise 2.5 M solution of n-BuLi in hexane (685 mL, 1 .71 mol) at -10°C. The resulting mixture was stirred at 0°C for 35 min. The mixture was cooled to -70°C and a solution of 2-fluoro-3-iodopyridine (I-26) (350 g, 1 .57 mol) in dry THF (1 L) was added. The mixture was stirred at -70°C for 2 hr. HCOOEt (128 g, 1 .73 mol) was added dropwise at -70°C. After the addition, the mixture was allowed to warm to room temperature and quenched with ice water (4 L). The mixture was diluted with EtOAc (4 L) and washed with brine (500 mL). The organic layer was dried over Na2S04 and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with petroleum:EtOAc = 10:1 to afford 2-fluoro-4-iodonicotinaldehyde (I-27) (180 g, 46percent) as a yellow solid.1H NMR (400 MHz, CDCI3) δ ppm 10.08 (s, 1 H), 7.91 (d, 1 H), 7.81 (d, 1 H).

Reference： [1] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[2] Patent: WO2016/97918, 2016, A1, . Location in patent: Page/Page column 58

2
[ 372-48-5 ]
[ 109-94-4 ]
[ 153034-82-3 ]

Reference： [1] Patent: WO2016/95204, 2016, A1, . Location in patent: Page/Page column 62

3
[ 168428-74-8 ]
[ 109-94-4 ]
[ 153034-82-3 ]

Reference： [1] Patent: WO2009/18656, 2009, A1, . Location in patent: Page/Page column 91

4
[ 153034-82-3 ]
[ 171366-19-1 ]

Reference： [1] Patent: WO2012/75383, 2012, A2, . Location in patent: Page/Page column 123

5
[ 153034-82-3 ]
[ 884494-51-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In water; <i>tert</i>-butyl alcohol at 20℃; for 1.25 h;	To a stirred solution of 2-fluoro-4-iodopyridine-3- carboxaldehyde (10.Og₅ 39.8 rnmol) in tert-butanol (350 mL) and water (100 niL) at room temperature were added 2-methyl-2-butene (42.1 ml, 398 mmol), sodium phosphate, monobasic, monohydrate (60.5 g, 438 mmol) and sodium chlorite (18.0 g, 199 mmol). The reaction mixture was stirred at room temperature for 75 min. The reaction mixture was diluted with dichloromethane and a 6M aqueous solution of hydrochloric acid was added until pH ~2. EPO <DP n="196"/>T/US2006/016344The water layer was extracted with dichloromethane. The organic phase was dried over MgSO₄, filtered and concentrated in vacuo. Purification by MPLC (CH₂Cl₂MeOH+ 1percent AcOH: 100/0 to 80/20) afforded 2-fluoro-4-iodonicotinic acid (10.63 g, 39.8 mmol, 100percent yield). MS (ESI pos. ion) m/z: 268 (MH+). Calc'd exact mass for C₆H₃FINO₂: 267.

Reference： [1] Patent: WO2006/116713, 2006, A1, . Location in patent: Page/Page column 194-195
[2] Patent: WO2016/95204, 2016, A1, . Location in patent: Page/Page column 62; 63

6
[ 153034-82-3 ]
[ 884494-84-2 ]

Reference： [1] Patent: WO2016/95204, 2016, A1,

[ 153034-82-3 ] Synthesis Path-Downstream 1~26

1
[ 146140-95-6 ]
[ 153034-82-3 ]
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