6374-91-0|5,7-Dibromoindoline-2,3-dione| Ambeed

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Quality Control of [ 6374-91-0 ] Purity: 95% SDS Specification

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Product Details of [ 6374-91-0 ]

CAS No. :	6374-91-0
Formula :	C₈H₃Br₂NO₂
M.W :	304.92
SMILES Code :	O=C1NC2=C(C=C(Br)C=C2Br)C1=O
MDL No. :	MFCD00034382
InChI Key :	QCTZEHIRXZGGSD-UHFFFAOYSA-N
Pubchem ID :	1809920

Safety of [ 6374-91-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 6374-91-0 ]

* 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.

Downstream synthetic route of [ 6374-91-0 ]

[ 6374-91-0 ] Synthesis Path-Downstream 1~35

1
[ 91-63-4 ]
[ 6374-91-0 ]
5,7-dibromo-3-[2]quinolylmethyl-3-hydroxy-indolin-2-one [ No CAS ]

References: [1]RSC Advances,2014,vol. 4,p. 19789 - 19793.
[2]Monatshefte fur Chemie,1912,vol. 33,p. 938.

2
[ 91-56-5 ]
[ 6374-91-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With bromine; acetic acid; at 70 - 80℃; for 1h;	In an Erlenmeyer flask, the isatin (1) 20 mmol (3.0 g)was solubilized in a mixture of acetic acid (70 mL)followed by addition of 47 mmol of bromine (7.5 g).The reaction mixture was heated at 70-80 C for 1 h.The progress of the reaction was monitored by thinlayer chromatography. After the total consumption ofthe starting material, the reaction medium was pouredonto ice and the precipitate formed was vacuum filtered.Subsequently the formed product was treated with 50 mLof 10 M HCl and redissolved.35 Orange solid; yield 70%;1H NMR (400 MHz, CDCl3 + DMSO-d6) δ 7.53 (s, 1H,H-6), 7.77 (s, 1H, H-4), 11.38 (s, 1H, NH); 13C NMR(100 MHz, CDCl3 + DMSO-d6) δ 106.55 (C), 115.60 (C),120.51 (C), 126.52 (CH), 142.23 (CH), 149.07 (C),159.19 (C), 183.02 (C); 13C NMR DEPT-135 (100 MHz,CDCl3 + DMSO-d6) δ 126.52 (CH), 142.23 (CH); IR (KBr)νmax / cm-1 3459, 3180, 3079, 1743, 1608, 1448, 1288, 873.
66%	With bromine; In ethanol; at 75℃; for 0.5h;Cooling with ice;	The synthesis of 5,7-dibromoisatin was based on the method of Kumar et al., 2013. Isatin (9.0 g, 61.2 mmol, 1 equiv) was warmed in ethanol (95 %, 100 mL) with stirring until it dissolved. Bromine (3.0 equiv, 16.3 g, 183.6 mmol, 9.4 mL) was added dropwise to the stirred isatin solution while maintaining the temperature of the reaction mixture between 70 C and 75 C. The solution was cooled to room temperature and placed on ice for 30 min. The resulting precipitate was washed with water and cold ethanol and then recrystallized from ethanol to yield bright orange-red crystals of 5,7-dibromoisatin (66 %), m.p.248 - 250 (lit.248-250 C).

References: [1]Chemistry of Natural Compounds,2004,vol. 40,p. 585 - 590.
[2]Russian Chemical Bulletin,2005,vol. 54,p. 988 - 991.
[3]Tetrahedron Letters,1997,vol. 38,p. 1501 - 1504.
[4]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 2963 - 2966.
[5]Journal of the Brazilian Chemical Society,2019,vol. 30,p. 198 - 209.
[6]Patent: WO2020/183307,2020,A1 .Location in patent: Page/Page column 34-35.
[7]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 931 - 938.
[8]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2919 - 2928.
[9]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 956 - 967.
[10]Patent: DE245042,1800,C .
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 10,p. 355.
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 10,p. 355.
[11]Journal of the American Chemical Society,1931,vol. 53,p. 317.
[12]Justus Liebigs Annalen der Chemie,1845,vol. 53,p. 12;.
    Journal de pharmacie et de chimie,vol. <3>7,p. 202.
[13]Organic Letters,2009,vol. 11,p. 3854 - 3857.
[14]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6006 - 6014.
[15]Medicinal Chemistry Research,2011,vol. 20,p. 587 - 594.
[16]Medicinal Chemistry Research,2011,vol. 20,p. 615 - 625.
[17]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 724 - 727.
[18]Angewandte Chemie - International Edition,2020,vol. 59,p. 11010 - 11019.
    Angew. Chem.,2020,vol. 132,p. 11103 - 11112,10.
[19]Patent: WO2020/219531,2020,A1 .Location in patent: Paragraph 0009.
[20]Chemical Papers,2021,vol. 75,p. 4793 - 4801.

3
[ 6374-91-0 ]
[ 74-88-4 ]
[ 106000-19-5 ]

References: [1]Organic Letters,2021,vol. 23,p. 1753 - 1757.
[2]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 345 - 352.
Khimiya Geterotsiklicheskikh Soedinenii,1987,vol. 23,p. 410 - 417.

4
[ 6374-91-0 ]
[ 67-64-1 ]
[ 188349-41-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With nitrogen-doped carbon nanodots; In water monomer; at 20℃; for 24h;	General procedure: A 4 mL glass vial was charged with the appropriate isatin 5a-f (0.1 mmol, 1 equiv.), NCDs-1 (0.9% w/v, 3.6 mg), theappropriate ketone 1e-h (0.7 mmol, 7 equiv.) and milli-Q water (final concentration: 0.25 M). The resulting mixture wasstirred for the indicated time (generally 6 hours) at ambient temperature. The reaction crude was then extracted with ethylacetate and the organic phase was filtered through sodium sulfate. The solvent was removed under reduced pressure and theresidue was purified by column chromatography (eluent: hexane/ethyl acetate) to give the corresponding α-functionalizedcarbonyl compounds 6a-i.

References: [1]Tetrahedron Letters,1997,vol. 38,p. 1501 - 1504.
[2]Tetrahedron,2002,vol. 58,p. 8399 - 8412.
[3]Chem,2020,vol. 6,p. 3022 - 3037.
[4]RSC Advances,2022,vol. 12,p. 6149 - 6165.

5
[ 6374-91-0 ]
[ 100-39-0 ]
[ 208592-60-3 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117.
[2]Synthetic Communications,1998,vol. 28,p. 1679 - 1689.

6
[ 6374-91-0 ]
[ 106-95-6 ]
1-allyl-5,7-dibromo-1H-indole-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		General procedure: A mixture of 7-bromoisatin (19) (250 mg, 1.11 mmol) and NaH (62.3 mg, 1.55 mmol) was dissolved in anhydrous DMF (6 mL) and stirred at rt for 20 min before the addition of KI (37.2 mg, 222 μmol) and allyl bromide (295 mg, 211 μL, 2.44 mmol). The reaction mixture was heated at 60 C and stirred at this temperature for 18 h. After cooling, EtOAc (25 mL) was added and the resulting solution was extracted with 0.5 M HCl (25 mL), followed by brine (25 mL). The orange organic layer was dried over MgSO4 and the solvent was removed by rotary evaporation to yield a sticky red residue. The resulting solid was purified by flash chromatography (100% DCM) to yield 13 as orange crystals (236 mg, 81%).

References: [1]Tetrahedron,2012,vol. 68,p. 6810 - 6819.
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117.
[3]Synthetic Communications,1998,vol. 28,p. 1679 - 1689.

7
[ 6374-91-0 ]
[ 98-86-2 ]
5,7-dibromo-3-hydroxy-3-(2-phenyl-2-oxoethyl)-2-oxindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water; at 20℃; for 2h;	General procedure: An aqueous solution of sodium hydroxide (5%, 10mL) was added slowly to the stirring solution of isatin (1mmol) and appropriate aryl acetophenone (1mmol) in ethanol (20mL) in 100mL conical flask. The stirring was continued for 2h and the completion of reaction was monitored by TLC. The reaction on completion was poured onto ice, solid obtained after filtration was crystallized from ethanol. The physical data for the characteristic compound is shown below:

References: [1]Tetrahedron,2002,vol. 58,p. 8399 - 8412.
[2]European Journal of Medicinal Chemistry,2014,vol. 85,p. 648 - 660.

8
[ 6374-91-0 ]
[ 51-35-4 ]
[ 16176-40-2 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 3295 - 3298.

9
[ 6374-91-0 ]
[ 824-94-2 ]
[ 620932-73-2 ]

References: [1]Organic Letters,2009,vol. 11,p. 3854 - 3857.
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117.

10
[ 6374-91-0 ]
[ 874-98-6 ]
5,7-dibromo-N-(m-methoxybenzyl)isatin [ No CAS ]