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Quality Control of [ 1145881-54-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1145881-54-4 ]

CAS No. :	1145881-54-4	MDL No. :	MFCD28789221
Formula :	C₆H₂F₂INO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZYLPUHQHTBTCBM-UHFFFAOYSA-N
M.W :	284.99	Pubchem ID :	58241682
Synonyms :

Safety of [ 1145881-54-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1145881-54-4 ]

* 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 [ 1145881-54-4 ]
Downstream synthetic route of [ 1145881-54-4 ]

[ 1145881-54-4 ] Synthesis Path-Upstream 1~1

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).

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

[ 1145881-54-4 ] Synthesis Path-Downstream 1~22

1
[ 446-35-5 ]
[ 1145881-54-4 ]

Yield	Reaction Conditions	Operation in experiment
90%		Synthesis of 1,3-difluoro-2-iodo-4-nitrobenzene (17c): 2,4-Difluoro-1-nitrobenzene 15 (159 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25 C. and the reaction mixture was then stirred at this temperature for 45 min according to TP 2. 12 (381 mg, 1.5 mmol) dissolved in dry THF (2 mL) was then dropwise added and the resulting mixture was stirred for 0.5 h. The reaction mixture was quenched with a sat. aq. Na2S2O3 solution (10 mL) and with a sat. aq. NH4CI solution (20 mL), extracted with diethyl ether (3×50 mL) and driedanhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:1) furnished compound 17c (256 mg, 90%) as a colourless solid. m.p.: 46.1-47.5 C.1H NMR (300 MHz, CDCl3) δ: 8.12-8.17 (m, 1 H), 7.04-7.08 (m, 1 H).13C NMR (75 MHz, CDCl3) δ: 165.6 (dd, J=5.0 Hz, J=252.6 Hz), 156.4 (dd, J=6.9 Hz, J=264.1 Hz), 127.7 (dd, J=2.3 Hz, J=10.3 Hz), 111.6 (dd, J=4.2 Hz, J=26.1 Hz), 74.3 (dd, J=29.2 Hz, J=1.9 Hz).MS (70 eV, El) m/z (%): 285 (100) [M+], 258 (17), 239 (19), 227 (17), 167 (25), 149 (66), 112 (58), 71 (11), 57 (12), 44 (12).IR (ATR) v (cm-1): 3098, 2926, 2855, 2359, 1916, 1739, 1602, 1584, 1529, 1463, 1425, 1336, 1301, 1277, 1218, 1147, 1105, 1011, 860, 827, 751, 698, 669, 621, 616.HRMS (El) for C6H2F2INO2 (284.9098): 284.9094.
74%	With (TMP)2Zn.MgCl2; iodine; In tetrahydrofuran; at 25℃;Inert atmosphere;	A dry, argon-filled Schlenk tube with a magnetic stirrer bar and septum is initially charged with 2,4- difluoro-1 -nitrobenzene (159 mg, 1 mmol) in anhydrous THF (2 ml). After adding (TMP^Zn.MgCh (3.00 ml, 1.2 mmol) at 25 C, the mixture is stirred for 30 min, then a solution of iodine (381 mg, 1.5 mmol) in anhydrous THF (2 ml) is added dropwise and the mixture is stirred at 25 C overnight. For workup, the mixture is diluted with aqueous sat. NH4CI solution (30 ml) and aqueous sat. Na2S203 solution (30 ml) and extracted with ethyl acetate (3 x 30 ml). After the combined organic phases have been dried over Na2S04, the solvent has been distilled off and purification has been effected by column chromatography on silica gel (heptane : ethyl acetate), the desired compound (210 mg, 74% of theory) was obtained as a colourless crystalline product. ¾ NMR (400 MHz, CDC13): δ in ppm = 8.15 (m, 1 H), 7.06 (m, 1 H)

Reference： [1]Organic Letters,2009,vol. 11,p. 1837 - 1840
[2]Patent: US2011/288296,2011,A1 .Location in patent: Page/Page column 13
[3]Patent: WO2013/120911,2013,A1 .Location in patent: Page/Page column 15

2
[ 1145881-54-4 ]
[ 1300014-98-5 ]

Reference： [1]Patent: US2011/105329,2011,A1

3
[ 1145881-54-4 ]
[ 1300014-99-6 ]

Reference： [1]Patent: US2011/105329,2011,A1

4
[ 1145881-54-4 ]
[ 124-41-4 ]
[ 1300014-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; for 16h;Reflux;	1,3-Difluoro-2-iodo-4-nitrobenzene (5.0 g, 17.5 mmol) was dissolved in 50 ml of methanol, and NaOMe (3.79 g, 70.1 mmol) was added. The solution was heated under reflux for 16 h. After concentration, the residue was chromatographed on silica gel using petroleum ether/ethyl acetate. This gave 2-iodo-1,3-dimethoxy-4-nitrobenzene (3 g) as a yellowish powder.1H-NMR (400 MHz, CDCl3): 8.0 (d, 1H); 6.88 (d, 1H); 3.96 (s, 3H); 3.91 (s, 3H)

Reference： [1]Patent: US2011/105329,2011,A1 .Location in patent: Page/Page column 37

5
[ 1145881-54-4 ]
[ 1300014-94-1 ]

Reference： [1]Patent: US2011/105329,2011,A1

6
[ 1145881-54-4 ]
[ 1300015-01-3 ]

Reference： [1]Patent: US2011/105329,2011,A1

7
[ 1426659-27-9 ]
[ 1145881-54-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1302 - 1305

8
[ 13697-89-7 ]
[ 1145881-54-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sulfuric acid; nitric acid; at 0 - 20℃;	To a solution of l,3-difluoro-2-iodobenzene (3.00g, 12.5mmol) in con.H2S04 (10 mL) was added nitric acid (98%) (1.91 g, 31.3mmol) at 0C and the resulting reaction mixture was stirred at room temperature for 4 min. The mixture was dropped into ice-water (80 mL), neutralized to pH=9 with aqueous NaOH (5%) and extracted with EtOAc. The extract was washed with brine, dried over Na2S04, filtered and concentrated in vacuo to afford the desired product (3.1g, 89%).1H NMR (CDC13): ? 8.12-8.17 (1H, m), 7.04-7.08 (1H, m).
89%	With sulfuric acid; nitric acid; at 0 - 20℃; for 4h;	To a solution of 1,3-difluoro-2-iodobenzene (3.00 g, 12.5 mmol) in concentrated sulfuric acid (10 mL) at 0 C was slowly added dropwise concentrated nitric acid (1.97 g, 31.3 mmol) and concentrated sulfuric acid LmL). Add 4 minutes at room temperature for 4 hours. Diluted with water reaction, 5% sodium hydroxide aqueous solution adjusted to pH 9, extracted with ethyl acetate. The resulting organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 2,4-difluoro-3-iodonitrobenzene (3.1g, 89%).
410 g	With sulfuric acid; potassium nitrate; at 0 - 15℃; for 4h;	a) 1,3-difluoro-2-iodo-6-nitrobenzene 1,3-Difluoro-2-iodobenzene (125 g) was added to sulfuric acid (500 mL) little by little at 0 C. Potassium nitrate (79 g) was added at 0 C. little by little, and the mixture was stirred at 0 C. for 30 min and at 15 C. for 3.5 hr. The same reaction using the same amounts was performed 4 times in total. The reaction mixtures were combined and added to ice water (1 L) at 0 C. 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 DCM (3 L). The obtained organic layer was washed with saturated brine (5 L), dried over sodium sulfate and concentrated to give the title compound (410 g). 1H NMR (400 MHz, DMSO-d6) δ 7.37-7.41 (1H, m), 8.28-8.32 (1H, m).

Reference： [1]Patent: WO2013/71865,2013,A1 .Location in patent: Page/Page column 56; 57
[2]Patent: CN103102349,2017,B .Location in patent: Paragraph 0497-0499
[3]Patent: US2019/169166,2019,A1 .Location in patent: Paragraph 0868; 0869

9
[ 372-18-9 ]
[ 1145881-54-4 ]

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

10
[ 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).

Reference： [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

11
[ 1145881-54-4 ]
[ 1392429-92-3 ]

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

12
[ 1145881-54-4 ]
[ 1437316-92-1 ]

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

13
[ 1145881-54-4 ]
5-chloro-N-(2,4-difluoro-3-(1H-pyrazolo[3,4-b]pyridin-5-ylethynyl)phenyl)-2-methoxypyridine-3-sulfonamide [ No CAS ]