1437316-91-0|2,4-Difluoro-3-iodoaniline| Ambeed

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Quality Control of [ 1437316-91-0 ] Purity: 97% SDS Specification

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Product Details of [ 1437316-91-0 ]

CAS No. :	1437316-91-0
Formula :	C₆H₄F₂IN
M.W :	255.00
SMILES Code :	NC1=CC=C(F)C(I)=C1F
MDL No. :	MFCD28789174
Boiling Point :	No data available
InChI Key :	GNVJNOOHMIVNAH-UHFFFAOYSA-N
Pubchem ID :	89579265

Safety of [ 1437316-91-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1437316-91-0 ]

* 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.

Upstream synthesis route of [ 1437316-91-0 ]
Downstream synthetic route of [ 1437316-91-0 ]

[ 1437316-91-0 ] Synthesis Path-Upstream 1~3

1
[ 1145881-54-4 ]
[ 1437316-91-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogenchloride; tin(II) chloride dihdyrate In water at 50℃; for 1 h;	To a solution of l,3-difluoro-2-iodo-4-nitrobenzene (1.14g, 4mmol) in con.HCl (4 mL) was added Satannous chloride dehydrate (2.71g, 12mmol) and the resulting reaction mixture was heated to 50°C for 1 hrs. The mixture was diluted with water, neutralized to pH=9 with aqueous NaOH (5percent) and extracted with CH₂C1₂. The extract was washed with brine, dried over Na₂S0₄, filtered and concentrated in vacuo to afford the desired product (0.93g, 91percent>).1H NMR (CDCI3): ? 6.70-6.93 (2H, m), 6.65 (2H, br).
91%	With hydrogenchloride; tin(II) chloride dihdyrate In water at 50℃; for 1 h;	To a mixture of 2,4-difluoro-3-iodonitrobenzene (1.14 g, 4 mmol) and tin dichloride dihydrate (2.71 g, 12 mmol) was slowly added dropwise concentrated hydrochloric acid (4 mL). Plus, heat to 50 ° C for 1 hour. Cooled, diluted with water reaction, 5percent sodium hydroxide aqueous solution adjusted to pH 9, extracted with dichloromethane. The resulting organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 2,4-difluoro-3-iodoaniline (0.93 g, 91percent).

References: [1] Patent: WO2013/71865, 2013, A1, . Location in patent: Page/Page column 57.
[2] Patent: CN103102349, 2017, B, . Location in patent: Paragraph 0501-0503.

2
[ 13697-89-7 ]
[ 1437316-91-0 ]

References: [1] Patent: WO2013/71865, 2013, A1, .
[2] Patent: CN103102349, 2017, B, .

3
[ 372-18-9 ]
[ 1437316-91-0 ]

References: [1] Patent: WO2013/71865, 2013, A1, .
[2] Patent: CN103102349, 2017, B, .

[ 1437316-91-0 ] Synthesis Path-Downstream 1~35

1
[ 13697-89-7 ]
[ 1437316-91-0 ]

References: [1]Patent: WO2013/71865,2013,A1 .
[2]Patent: CN103102349,2017,B .
[3]Patent: US2019/169166,2019,A1 .

2
[ 372-18-9 ]
[ 1437316-91-0 ]

References: [1]Patent: WO2013/71865,2013,A1 .
[2]Patent: CN103102349,2017,B .

3
[ 1145881-54-4 ]
[ 1437316-91-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogenchloride; tin(II) chloride dihdyrate; In water; at 50℃; for 1.0h;	To a solution of l,3-difluoro-2-iodo-4-nitrobenzene (1.14g, 4mmol) in con.HCl (4 mL) was added Satannous chloride dehydrate (2.71g, 12mmol) and the resulting reaction mixture was heated to 50C for 1 hrs. The mixture was diluted with water, neutralized to pH=9 with aqueous NaOH (5%) and extracted with CH2C12. The extract was washed with brine, dried over Na2S04, filtered and concentrated in vacuo to afford the desired product (0.93g, 91%>).1H NMR (CDCI3): ? 6.70-6.93 (2H, m), 6.65 (2H, br).
91%	With hydrogenchloride; tin(II) chloride dihdyrate; In water; at 50℃; for 1.0h;	To a mixture of 2,4-difluoro-3-iodonitrobenzene (1.14 g, 4 mmol) and tin dichloride dihydrate (2.71 g, 12 mmol) was slowly added dropwise concentrated hydrochloric acid (4 mL). Plus, heat to 50 C for 1 hour. Cooled, diluted with water reaction, 5% sodium hydroxide aqueous solution adjusted to pH 9, extracted with dichloromethane. The resulting organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 2,4-difluoro-3-iodoaniline (0.93 g, 91%).
165 g	With hydrogenchloride; tin(II) chloride dihdyrate; In ethanol; at 15 - 100℃;	b) 2,4-difluoro-3-iodoaniline Concentrated hydrochloric acid (321 mL) was added to a solution of 1,3-difluoro-2-iodo-6-nitrobenzene (300 g) in ethanol (1 L) at 15 C. Tin chloride dihydrate (948 g) was added at 15 C. little by little, and the mixture was stirred at 100 C. for 2 hr. The reaction mixture was added to ice water (1 L) at 0 C., and a saturated aqueous sodium hydroxide solution was added to adjust the pH to 9. The mixture was filtered, and the filtrate was extracted twice with ethyl acetate (600 mL). The obtained organic layer was dried over sodium sulfate and concentrated to give the title compound (165 g). 1H NMR (400 MHz, DMSO-d6) delta 5.17 (2H, s), 6.76-6.81 (2H, m).

References: [1]Patent: WO2013/71865,2013,A1 .Location in patent: Page/Page column 57.
[2]Patent: CN103102349,2017,B .Location in patent: Paragraph 0501-0503.
[3]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 0870; 0871.

4
[ 1437316-91-0 ]
[ 1437316-92-1 ]

References: [1]Patent: WO2013/71865,2013,A1 .
[2]Patent: CN103102349,2017,B .

5
[ 10147-36-1 ]
[ 1437316-91-0 ]
[ 1392429-92-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With pyridine; In 1,2-dichloro-ethane; for 2.0h;Reflux;	N-(2,4-difluoro-3-iodophenyl)propane-l -sulfonamideTo a solution of <strong>[1437316-91-0]2,4-difluoro-3-iodoaniline</strong> (255mg, lmmol) in 1,2-dichloroethane (3 mL) was added pyridine (lmL), followed by propane- 1-sulfonyl (157mg, 1. lmmol) and the resulting reaction mixture was heated to refluxing for 2 hrs. The solvent was removed in vacuo. The residue was dissolved in EtOAc, washed with aqueous NaHC03, brine, dried over Na2S04, filtered and concentrated in vacuo to afford the desired product (298mg, 83%>).1H NMR (CDCI3): ? 7.56-7.58 (1H, m), 6.90-6.95 (1H, m), 6.44 (1H, br), 3.03-3.07 (2H, m),1.84-1.90 (2H, m), 1.03-1.07 (3H, m).
83%	With pyridine; In 1,2-dichloro-ethane; for 2.0h;Reflux;	To a solution of <strong>[1437316-91-0]2,4-difluoro-3-iodoaniline</strong> (255 mg, 1 mmol) in 1,2_dichloroethane (3 mL) was slowly added dropwise a solution of P to pyridine (lmL), propylsulfonyl chloride (157 mg, 1. lmmol). The reaction solution was heated under reflux for 2 hours, cooled and concentrated in vacuo to remove the solvent. The resulting oil was dissolved in ethyl acetate (20 mL) and washed with 5% sodium bicarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give N- (2,4-difluoro-3- Iodophenyl) propane-1-sulfonamide (298 mg, 83%).

References: [1]Patent: WO2013/71865,2013,A1 .Location in patent: Page/Page column 57.
[2]Patent: CN103102349,2017,B .Location in patent: Paragraph 0505-0507.

6
[ 1437316-91-0 ]
5-chloro-N-(2,4-difluoro-3-(1H-pyrazolo[3,4-b]pyridin-5-ylethynyl)phenyl)-2-methoxypyridine-3-sulfonamide [ No CAS ]