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Chemistry
Heterocyclic Building Blocks
Indoles
5,7-Dibromoindoline-2,3-dione
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Indoles
Indolines Bromides Amides Ketones

[ CAS No. 6374-91-0 ]

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 6374-91-0
Chemical Structure| 6374-91-0
Chemical Structure| 6374-91-0
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Quality Control of [ 6374-91-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 6374-91-0 ]

Product Details of [ 6374-91-0 ]

CAS No. :6374-91-0 MDL No. :MFCD00034382
Formula : C8H3Br2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QCTZEHIRXZGGSD-UHFFFAOYSA-N
M.W :304.92 Pubchem ID :1809920
Synonyms :

Calculated chemistry of [ 6374-91-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.56
TPSA : 46.17 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 2.1
Log Po/w (WLOGP) : 1.77
Log Po/w (MLOGP) : 1.62
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 1.97

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.4
Solubility : 0.123 mg/ml ; 0.000403 mol/l
Class : Soluble
Log S (Ali) : -2.7
Solubility : 0.608 mg/ml ; 0.002 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.47
Solubility : 0.0104 mg/ml ; 0.000034 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.81

Safety of [ 6374-91-0 ]

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 [ 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   1~69

  • 1
  • [ 91-63-4 ]
  • [ 6374-91-0 ]
  • 5,7-dibromo-3-[2]quinolylmethyl-3-hydroxy-indolin-2-one [ No CAS ]
Reference： [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 ]
YieldReaction ConditionsOperation 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).
Reference： [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 ]
Reference： [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 ]
YieldReaction ConditionsOperation 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.
Reference： [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 ]
Reference： [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 ]
YieldReaction ConditionsOperation 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%).
Reference： [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
  • 8
  • [ 6374-91-0 ]
  • [ 98-86-2 ]
  • 5,7-dibromo-3-hydroxy-3-(2-phenyl-2-oxoethyl)-2-oxindole [ No CAS ]
YieldReaction ConditionsOperation 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:
Reference： [1]Tetrahedron,2002,vol. 58,p. 8399 - 8412
[2]European Journal of Medicinal Chemistry,2014,vol. 85,p. 648 - 660
  • 9
  • [ 6374-91-0 ]
  • [ 51-35-4 ]
  • [ 16176-40-2 ]
Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 3295 - 3298
  • 10
  • [ 6374-91-0 ]
  • [ 824-94-2 ]
  • [ 620932-73-2 ]
Reference： [1]Organic Letters,2009,vol. 11,p. 3854 - 3857
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 11
  • [ 6374-91-0 ]
  • [ 874-98-6 ]
  • 5,7-dibromo-N-(m-methoxybenzyl)isatin [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 12
  • [ 6374-91-0 ]
  • [ 100-11-8 ]
  • 5,7-dibromo-1-(4-nitrobenzyl)indoline-2,3-dione [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
[2]Angewandte Chemie - International Edition,2013,vol. 52,p. 8299 - 8303
    Angew. Chem.,2013,vol. 125,p. 8457 - 8461,5
  • 13
  • [ 6374-91-0 ]
  • [ 3958-60-9 ]
  • 5,7-dibromo-N-(o-nitrobenzyl)isatin [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 14
  • [ 6374-91-0 ]
  • [ 104-83-6 ]
  • 5,7-dibromo-N-(p-chlorobenzyl)isatin [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 15
  • [ 6374-91-0 ]
  • [ 589-15-1 ]
  • 5,7-dibromo-N-(p-bromobenzyl)isatin [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 16
  • [ 6374-91-0 ]
  • [ 16004-15-2 ]
  • 5,7-dibromo-N-(p-iodobenzyl)isatin [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 17
  • [ 6374-91-0 ]
  • [ 402-49-3 ]
  • 5,7-dibromo-N-(p-trifluoromethylbenzyl)isatin [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 18
  • [ 6374-91-0 ]
  • [ 6482-24-2 ]
  • 5,7-dibromo-N-(2'-methoxyethyl)isatin [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 19
  • [ 6374-91-0 ]
  • [ 2417-72-3 ]
  • 4-[(5,7-dibromo-2,3-dihydro-2,3-dioxo-1H-indol-1-yl)methyl]benzoic acid methyl ester [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 20
  • [ 6374-91-0 ]
  • [ 18880-00-7 ]
  • 5,7-dibromo-N-(p-tertbutylbenzyl)isatin [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 21
  • [ 6374-91-0 ]
  • [ 4392-24-9 ]
  • C17H11Br2NO2 [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 22
  • [ 6374-91-0 ]
  • [ 2567-29-5 ]
  • 5,7-dibromo-N-(p-phenylbenzyl)isatin [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 23
  • [ 6374-91-0 ]
  • [ 107-82-4 ]
  • 5,7-dibromo-N-(3'-methylbutyl)isatin [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 24
  • [ 6374-91-0 ]
  • [ 104-81-4 ]
  • [ 620932-72-1 ]
Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5109 - 5117
  • 25
  • [ 132122-34-0 ]
  • [ 6374-91-0 ]
  • 5,7-Dibromo-3-(5,7-di-tert-butyl-2-oxo-benzofuran-3-ylidene)-1,3-dihydro-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In methanol; acetic acid; Example 8 5,7-Dibromo-3-(5,7-di-tert-butyl-2-oxo-benzofuran-3-ylidene)-1,3-dihydro-indol-2-one (Z/E mixture) 7.6 g (0.025 mol) of 5,7-dibromoisatin (prepared analogously to the method described in Collect. Czech. Chem. Commun., 55 (1990) 2963), 5.5 g (0.025 mol) of 7-tert-butyl-5-methoxy-3H-benzofuran-2-one and 0.25 g of p-toluenesulfonic acid are boiled in 25 ml of acetic acid under nitrogen for 17 hours. 40 ml of methanol are then added and the suspension obtained is cooled to 5 C. The precipitated solid is filtered off and the filter residue is washed with methanol and dried at 60 C. The yield is 11.9 g (94% of theory). Melting point: 232-256 C. C: calculated/found 54.06/54.35; H: calculated/found 4.35/4.22; N: calculated/found 2.63/2.57
Reference： [1]Patent: US6503937,2003,B1
  • 26
  • [ 6374-91-0 ]
  • [ 4636-16-2 ]
  • [ 1020265-02-4 ]
YieldReaction ConditionsOperation in experiment
Example 43; 5, 7-Dibromo-l-(2-oxo-2-phenylethyl)-lH-indole-2, 3-dione (43); <n="59"/>A mixture of KI (113 mg, 0.68 mmol) and phenacyl bromide (68.0 nig, 0.34 mniol) was dissolved in anhydrous DMF (0.5 mL) and stirred at -5 0C under nitrogen for 5 h, followed by cooling in a freezer at -18 C for 20 h.24 A mixture of the 5,7-dibromoisatin (103 mg, 0.34 mmol) and K2CO3 (47.0 mg, 0.34 mmol) or NaH (13.7 mg, 0.34 mmol) was dissolved in anhydrous DMF (5 mL) and stirred under nitrogen at 4 0C for 3 h. This anion solution was added in portions (0.5 mL) to the phenacyl iodide maintained at -2 C such that each portion had reacted before the addition of the next portion (monitored by TLC). The yellow/brown reaction mixture was stirred at RT for 25 h but no change in colour intensity was observed after 2 h. To the resulting solution was added water (60 mL) and 1 M HCl (2 mL) to acidify to pH 1. The suspension was filtered and the precipitate washed with water. The resulting solid was purified by flash chromatography on silica gel (DCM) to yield the title compound (13.5 mg, 9 %) as bright red/orange crystals, m.p. 173-175 0C, Rf 0.58 (silica, DCM). 1H NMR (500 MHz): δ 5.64 (s, 2H, Hl'), 7.54 (t, J = 7.5 Hz5 2H, H3", H5"), 7.67 (t, J= 7.5 Hz, IH, H4")5 7.75 (d, J= 2 Hz, IH, H4), 7.80 (d, J= 2 Hz, IH, H6), 8.00 (d, J= 7.5 Hz, 2H, H2", H6"). 13C NMR (126 MHz): δ 48.2, 105.4, 117.1, 121.3, 126.5, 127.6, 128.3% 129.1a, 134.4, 144.8, 146.9, 158.2, 180.8, 191.3. HREI-MS: m/z calcd for C16H9NO3 79Br81Br [M+]: 422.8929; found 422.8928.
Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3118 - 3124
[2]Patent: WO2008/74078,2008,A1 .Location in patent: Page/Page column 57-58
  • 27
  • [ 6374-91-0 ]
  • [ 2146-61-4 ]
  • [ 1020264-98-5 ]
YieldReaction ConditionsOperation in experiment
45% With potassium iodide In N,N-dimethyl-formamide at 50℃; for 18h;
Reference： [1]Matesic, Lidia; Locke, Julie M.; Bremner, John B.; Pyne, Stephen G.; Skropeta, Danielle; Ranson, Marie; Vine, Kara L. [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 6, p. 3118 - 3124]
  • 28
  • [ 6374-91-0 ]
  • [ 14425-64-0 ]
  • [ 1020264-99-6 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3118 - 3124
  • 29
  • [ 6374-91-0 ]
  • [ 1746-28-7 ]
  • [ 1020264-97-4 ]
YieldReaction ConditionsOperation in experiment
50% With potassium iodide In N,N-dimethyl-formamide at 50℃; for 18h;
Reference： [1]Matesic, Lidia; Locke, Julie M.; Bremner, John B.; Pyne, Stephen G.; Skropeta, Danielle; Ranson, Marie; Vine, Kara L. [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 6, p. 3118 - 3124]
  • 30
  • [ 6374-91-0 ]
  • [ 40422-70-6 ]
  • [ 1020264-96-3 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3118 - 3124
  • 31
  • [ 6374-91-0 ]
  • [ 103-63-9 ]
  • [ 1020264-95-2 ]
YieldReaction ConditionsOperation in experiment
32% Example 36; 5, 7-Dibromo-l-phenethyl-lH-indole-2,3-dione (36); A mixture of 5,7-dibromoisatin (200 mg, 0.66 mmol) and K2CO3 (128 mg, 0.92 mmol) or NaH (36.8 mg, 0.92 mmol) was dissolved in anhydrous DMF (4 mL) and stirred under nitrogen at 4 0C for 3 h (or 20 min at RT for NaH) before the addition of KI (22.0 mg, 0.13 mmol) and (2-bromoethyl)benzene (270 mg, 0.2 mL, 1.46 mmol). The reaction mixture was heated at 50 C and stirred at this temperature for 18 h. To the resulting solution was added water (80 mL) and 1 M HCl (2 mL) to acidify to pH 1. The suspension was filtered and the precipitate washed with water. The resulting solid was purified by <n="56"/>flash chromatography on silica gel (CHCI3) to yield the title compound (86.3 mg, 32 %) as bright red crystals, m.p. 165-168 C, Rf 0.71 (silica, DCM). 1H NMR (500 MHz): δ 3.03 (t, J= 8 Hz, 2H, H2'), 4.39 (t, J= 8 Hz, 2H, Hl '), 7.30 (m, 5H, H2"- H6"), 7.69 (d, J= 1.5 Hz, IH, H4), 7.89 (d, J= 1.5 Hz, IH, H6). 13C NMR (126 MHz): δ 35.0, 42.4, 104.5, 116.6, 121.1, 126.7, 127.2, 128.4a, 128.6a, 136.7, 144.8, 146.4, 157.5, 181.1. HREI- MS: m/z calcd for Ci6HnNO279Br81Br [M+]: 406.9157; found 406.9166.
Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3118 - 3124
[2]Patent: WO2008/74078,2008,A1 .Location in patent: Page/Page column 54-55
  • 32
  • [ 6374-91-0 ]
  • [ 99-73-0 ]
  • [ 1020265-04-6 ]
YieldReaction ConditionsOperation in experiment
5% Example 45; 5, 7-Dibromo-l-[2-(4-bromophenyl)-2-oxo-ethyl]-lH-indole-2, 3-dione (45); <strong>[6374-91-0]5,7-Dibromoisatin</strong> (153 mg, 0.5 mmol) and NaH (20.0 mg, 0.5 mmol) was dissolved in anhydrous DMF (1.25 mL) and stirred at RT under nitrogen for 20 min before the addition of freshly distilled trimethylsilyl chloride (81.0 mg, 0.095 mL, 1.5 mmol).26 The reaction mixture was heated at 50 0C and stirred at this temperature for 1 h before the addition of 4-bromophenacyl bromide (139 mg, 0.5 mmol) and further heating at 100 C for 1.5 h. Upon cooling, water (15 mL) was added, the suspension was filtered and the precipitate washed with hot water (90 0C) to yield a rust coloured compound. The product was recrystallized from glacial AcOH, filtered and washed with ice cold water to yield the title compound (11.2 mg, 5 %) as a light yellow powder, m.p. 184-186 C, Rf 0.65 (silica, DCM). 1H NMR (500 MHz): δ 5.60 (s, 2H, Hl '), 7.70 (d, J = 8.5 Hz, 2H, H3", H5")5 7.76 (d, J= 2 Hz, IH, H4), 7.80 (d, J= 2 Hz, IH, H6), 7.87 (d, J= 8.5 Hz, 2H, H2", H6"). 13C NMR (126 MHz): δ 47.9, 105.3, 117.2, 121.3, 127.6, 129.6a, 129.8, 132.5a, 132.5, 144.7, 146.7, 158.1, 180.7, 190.4. HREI-MS: m/z calcd for C]6H8NO3 79Br81Br81Br [M+]: 502.8013; found 502.8007.
Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3118 - 3124
[2]Patent: WO2008/74078,2008,A1 .Location in patent: Page/Page column 59
  • 33
  • [ 6374-91-0 ]
  • [ 939-26-4 ]
  • [ 1020265-01-3 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3118 - 3124
  • 34
  • [ 6374-91-0 ]
  • [ 86-52-2 ]
  • [ 1020265-00-2 ]
YieldReaction ConditionsOperation in experiment
62% Example 41; 5, 7-Dibromo-l-(l-naphthylmefhyl)-lH-indole-2, 3-dione (41); <n="58"/>A mixture of 5,7-dibromoisatin (101 mg, 0.33 mmol) and NaH (18.0 mg, 0.46 mmol) was dissolved in anhydrous DMF (2.5 mL) and stirred under nitrogen at RT for 20 min before the addition of KI (l l.O mg, 0.066 mmol) and 1 -chloromethylnaphthalene (128 mg, 0.11 mL, 0.73 mmol). The reaction mixture was heated at 60 C and stirred at this temperature for 19 h. After cooling, ethyl acetate (5O mL) was added and the resulting solution was extracted with 0.5 M HCl (50 mL) followed by brine (50 mL). The orange organic layer was dried over MgSO4 and the solvent was removed to yield a sticky red/orange residue. The resulting solid was purified by flash chromatography on silica gel [DCM:PS (3:2)] to yield the title compound (90.8 mg, 62 %) as dark red crystals, m.p. 218-219 0C5 Rf 0.35 (silica, DCM). 1H NMR (500 MHz): δ 5.81 (s, 2H, Hl'), 7.06 (d, J= 7 Hz, IH, H2"), 7.34 (t, J= 7.5 Hz5 IH, H3"), 7.53 (t, J= 7 Hz5 IH5 H6"), 7.58 (t, J= 7 Hz5 IH, H7"), 7.76 (m, 3H5 H4, H6, H4") 7.88 (d, J= 8.5 Hz, IH, H5"), 7.93 (d5 J= 8.5 Hz5 IH5 H8"). 13C NMR (126 MHz): 5 42.8, 105.5, 117.1, 121.3, 121.4, 122.I5 125.3, 126.0, 126.6, 127.5, 128.0, 129.0, 129.8, 130.7, 133.8, 145.3, 146.8, 158.1, 181.2. HREI-MS: m/z calcd for C19HnNO279Br81Br [M+]: 444.9136; found 444.9131.
Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3118 - 3124
[2]Patent: WO2008/74078,2008,A1 .Location in patent: Page/Page column 56-57
  • 35
  • [ 6374-91-0 ]
  • 1-allyl-5,7-dibromo-1H-indole-2,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% General Method I: N-Alkylation oflsatins; Alkylation of the isatins was carried out using a general method based on that of Torres (Garden, S. J.; Torres, J. C; da Silva, L. E.; Pinto, A. C. Synth. Commun. 1998, 28, 1679- 1689). The appropriate isatin (1 equiv) was taken up in anhydrous DMF (~ 1 mL per 0.1 mmol of isatin) and cooled on ice with stirring. Solid K2CO3 (1.4 equiv) or Cs2CO3 (1.4 equiv.) was added in one portion and the dark-coloured suspension was brought to rt and stirred for a further 2 h. The appropriate alkylating agent, typically a halide such as a benzyl halide (1.1 equiv.) and KI (0.2 equiv.) were added and the reaction mixture stirred at 80 C for 5 - 16 h, until all the isatin starting material had been consumed (tic). The reaction mixture was tipped into HCl (0.5 M) and extracted with ethyl acetate (1 x 50 mL). The ethyl acetate layer was washed with brine and dried over MgSO4. The solvent was removed and the crude product was purified using flash column chromatography with isocratic elution with DCM unless otherwise stated.; Example 1; N-allyl-5, 7-dibromoisatin (1); The product was a bright red solid (102 mg, 45%), mp 103 - 105 C, Rf 0.45 (DCM, silica). 1H NMR (CDCl3, 500 MHz) δ 4.79 (d, J= 5 Hz, 2H, CH2), 5.23 (d, J= 17 Hz, IH,f <n="42"/>CEcisHtrms), 5.26 (d, J= IO Hz, IH, CNo.efeHtrans), 5.96 (ddt, J= 5, 10, 17 Hz, IH, CH), 7.70 (d, J = 2 Hz, IH, H4), 7.86 (d, J = 2 Hz, IH, H6). 13C NMR (CDCl3, 126 MHz) δ 43.1, 104.9, 116.8, 117.6, 121.1, 127.3, 131.4, 145.1, 146.6, 157.7, 181.2. LREI-MS m/z 343/345/347 ([M]+/([M+2]+/[M+4]+) (Garden, S. J.; Torres, J. C; da Silva, L. E.; Pinto, A. C. Synth Commun. 1998, 28, 1679-1689).
Reference： [1]Patent: WO2008/74078,2008,A1 .Location in patent: Page/Page column 40-41
  • 36
  • [ 6374-91-0 ]
  • [ 389062-34-4 ]
  • [ 1034766-44-3 ]
YieldReaction ConditionsOperation in experiment
43% Example 49; Synthesis of 5, 7-Dibromo-N-[4 '-(tributylstannyl)benzyl]isatin (49); <n="62"/><strong>[6374-91-0]5,7-Dibromoisatin</strong> (100 mg, 0.33 mmol) and K2CO3 (63 mg, 0.46 mmol) were suspended in dry DMF (5 mL) and the mixture stirred at 0-5 0C for 30 min. 4-(Tributylstannyl)benzyl chloride (150 mg, 0.36 mmol) and KI (11 mg, 0.07 mmol) were added and the suspension stirred at 80 C for 16 h. The reaction mixture was poured into HCl (0.5 M, 25 mL) and then extracted with ethyl acetate (1 x 25 mL) and the ethyl acetate layer washed with brine and dried over MgSO4, The solvent was removed and the residue was purified using flash column chromatography, eluting with 1 : 1 DCM/pet spirit. The product was a bright red semi-solid that solidified on standing (97 mg, 43%), mp 111 - 113 0C, Rf 0.39 (1 :1 DCM/pet spirit, silica). 1H NMR D 0.87 (t, J = 7 Hz, 9H, H4"), 1.03 (m, 6H, Hl"), 1.31 (m, 6H, H3"), 1.52 (m, 6H, H2"), 5.39 (s, 2H, Hl '), 7.19 (d, J= 8 Hz5 2H, H3'), 7.41 (d, J = 8 Hz, 2H, H4'), 7.71 (d, J= 2 Hz, IH, H4), 7.81 (d, J= 2 Hz, IH3 H6). A minor signal at D7.41 (dd, J= 8, 37 Hz, H4') due to coupling of H4' with Sn was also observed. 13C NMR δ 9.6 (Cl"), 13.6 (C4"), 27.3 (C3"), 29.0 (C2"), 44.7 (Cl'), 105.3, 117.1, 121.4, 125.9 (C3'), 127.5, 135.2, 136.9 (C4'), 141.6, 145.3, 146.8, 158.3 (C2), 181.3 (C3). LREI-MS m/z 570 ([M-C8H18]+); HREI-MS m/z calcd for [M]+ C27H3581Br2NO2118Sn: 685.001, found: 685.000.
Reference： [1]Patent: WO2008/74078,2008,A1 .Location in patent: Page/Page column 60-61
  • 37
  • [ 6374-91-0 ]
  • [ 217300-17-9 ]
  • [ 1185745-40-7 ]
Reference： [1]Organic Letters,2009,vol. 11,p. 3854 - 3857
  • 38
  • [ 6374-91-0 ]
  • [ 99-90-1 ]
  • [ 1192111-99-1 ]
YieldReaction ConditionsOperation 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:
Reference： [1]Green Chemistry,2009,vol. 11,p. 1465 - 1476
[2]European Journal of Medicinal Chemistry,2014,vol. 85,p. 648 - 660
  • 39
  • [ 6374-91-0 ]
  • [ 67-64-1 ]
  • [ 1261038-55-4 ]
  • (S)-5,7-dibromo-3-hydroxy-3-(2-oxopropyl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The organocatalyst 2 (7 mg, 0.03mmol)) was stirred in 1 mL acetone and 2 mL THF for 10 min at-35 C. The corresponding isatin 7a(0.3 mmol) was added and the mixture was stirred for 48 h. Then acetone was removed under reduced pressure and the mixture was purified by flash column chromatography on silica gel (petroleum ether / ethyl acetate (2:1)). (S)-5,7-Dibromo-3-hydroxy-3-(2-oxopropyl)indolin-2-one(Table 4, entry 10)2; [α]D25= -7.8 (c0.26 in MeOH, 51%ee). IR (film):n= 3271, 2924, 1729, 1616, 1461 cm-1.1H NMR (400 MHz, CDCl3+DMSO):δ= 9.58(s, 1H) 7.26-7.24 (m, 1H), 7.12-7.10 (m, 1H), 5.77 (s, 1H), 3.05-2.93(m, 2H), 1.89 (s, 3H) ppm.Theeewas determined by HPLC (Chiralpak AD-H column, hexane/i-PrOH 80:20, flow rate 1 mL/min; tR(major) = 8.0 min; tR(minor) = 9.2 min,λ= 254 nm).
Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 9460 - 9464
[2]Tetrahedron Asymmetry,2016,vol. 27,p. 463 - 466
[3]RSC Advances,2022,vol. 12,p. 6149 - 6165
  • 40
  • [ 61550-02-5 ]
  • [ 6374-91-0 ]
  • 5,7-dibromo-3-hydroxy-3-(5-oxo-2,5-dihydrofuran-2-yl)indolin-2-one [ No CAS ]
  • 5,7-dibromo-3-hydroxy-3-(5-oxo-2,5-dihydrofuran-2-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of isatin 1 (1 mmol) in THF (2 mL) was added La(OTf)3 (5 mol %). The mixture was cooled to -78 C and stirred at this temperature for 15 min. Then the solution of 2-(trimethylsilyloxy)furan 2 (1.5 mmol) in THF (1 mL) was added dropwise. The mixture was stirred at -78 C for 2 h. Later the mixture was brought to 20 C and stirred for additional 0.5-1.5 h (Table 1). The reaction was monitored by TLC. After the completion of the reaction it was diluted with tetrahydrofuran (2.0 mL) and quenched with 10% aqueous HCl (1.0 mL). The mixture was stirred for 0.25 h at room temperature, neutralized by the addition of a saturated aqueous NaHCO3 solution, and extracted with ethyl acetate (3×5 mL). The combined organic layer washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography (ethyl acetate/hexanes). The inseparable diastereomers threo/erythro ratio of the product was determined by 1H NMR analysis of the crude reaction mixture.
Reference： [1]Tetrahedron,2011,vol. 67,p. 3150 - 3155
  • 41
  • [ 6374-91-0 ]
  • [ 762-72-1 ]
  • [ 1309578-02-6 ]
Reference： [1]Organic Letters,2011,vol. 13,p. 6398 - 6401
[2]Chemistry Letters,2011,vol. 40,p. 357 - 359
  • 42
  • [ 6940-78-9 ]
  • [ 6374-91-0 ]
  • [ 1344698-20-9 ]
YieldReaction ConditionsOperation in experiment
75% General procedure: 5,7-dibromoisatin 2 (1 g, 3.28 mmol) was taken up in anhydrous DMF (30 mL) and cooled on ice with stirring. Solid K2CO3 (544 mg, 3.94 mmol) was added in one portion, and the dark colored suspension was brought to room temperature and stirred for a further 1 h. 1-Bromo-3-chloropropane (620 mg, 3.94 mmol, 0.387 mL) was added slowly with constant stirring and the reaction mixture was stirred at 80 C for 4-8 h, until the 5,7-dibromoisatin starting material had been consumed (TLC). The reaction mixture was poured into HCl (0.5 M, 50 mL) and extracted with ethyl acetate (3 × 50 mL). The ethyl acetate layer was washed with brine and dried over MgSO4. The solvent was removed, and the crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to give pure 3 (0.93 g, 74%) as orange red crystals.
Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6006 - 6014
  • 43
  • [ 623-24-5 ]
  • [ 6374-91-0 ]
  • [ 1344698-26-5 ]
YieldReaction ConditionsOperation in experiment
75% General procedure: 5,7-dibromoisatin 2 (1 g, 3.28 mmol) was taken up in anhydrous DMF (30 mL) and cooled on ice with stirring. Solid K2CO3 (544 mg, 3.94 mmol) was added in one portion, and the dark colored suspension was brought to room temperature and stirred for a further 1 h. 1-Bromo-3-chloropropane (620 mg, 3.94 mmol, 0.387 mL) was added slowly with constant stirring and the reaction mixture was stirred at 80 C for 4-8 h, until the 5,7-dibromoisatin starting material had been consumed (TLC). The reaction mixture was poured into HCl (0.5 M, 50 mL) and extracted with ethyl acetate (3 × 50 mL). The ethyl acetate layer was washed with brine and dried over MgSO4. The solvent was removed, and the crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to give pure 3 (0.93 g, 74%) as orange red crystals.
General procedure: Initially, mono (5 or 7) or di-substituted (5,7) or unsubstitutedisatins 1(ael) (10 mmol) were dissolved in anhydrous DMF (30 mL)and cooled on ice with stirring. Solid dry K2CO3 (11 mmol) wasadded in one portion, and the dark-colored suspensionwas broughtto room temperature and stirred for a further 1 h. 1,4-bis(bromomethyl)benzene (40 mmol) was added slowly withconstant stirring until the mono or di-substituted isatin startingmaterial had been consumed (TLC). The reaction mixture waspoured into cold water and extracted with ethyl acetate. The ethylacetate layer was washed with water, brine, and dried over MgSO4.The solvent was removed, and the crude product was purified bysilica gel column chromatography using (hexanes/EtOAc, 80:20) aseluent to yield the key intermediates (-N-(p-bromomethyl benzyl)isatins 2(ael) (yield 75-80%) as orange-red crystals.
5,7-dibromoisatin (10 mmol) was dissolved in anhydrous DMF (30 mL) and cooled on ice with stirring. Solid K2CO3 (11 mmol) was added and the dark-colored suspension was brought to room temperature and stirred for 1 hour. 1,4-bis(bromomethyl)benzene (40 mmol) was added slowly with constant stirring until the starting material had been consumed (monitored by TLC). The reaction mixture was poured into cold water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine and dried over MgSO4. The solvent was removed, and the crude product was purified by silica gel column chromatography using (hexanes/ethyl acetate, 80:20) as the eluent to yield the intermediate 5,7-dibromo-1-(4- bromomethylbenzyl)-1H-indole-2,3-dione as orange-red crystals.
Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6006 - 6014
[2]European Journal of Medicinal Chemistry,2020,vol. 187
[3]Patent: WO2021/252749,2021,A1 .Location in patent: Paragraph 00173
  • 44
  • [ 6374-91-0 ]
  • [ 83948-53-2 ]
  • [ 1354973-83-3 ]
YieldReaction ConditionsOperation in experiment
62% General procedure: 5,7-dibromoisatin 2 (1 g, 3.28 mmol) was taken up in anhydrous DMF (30 mL) and cooled on ice with stirring. Solid K2CO3 (544 mg, 3.94 mmol) was added in one portion, and the dark colored suspension was brought to room temperature and stirred for a further 1 h. 1-Bromo-3-chloropropane (620 mg, 3.94 mmol, 0.387 mL) was added slowly with constant stirring and the reaction mixture was stirred at 80 C for 4-8 h, until the 5,7-dibromoisatin starting material had been consumed (TLC). The reaction mixture was poured into HCl (0.5 M, 50 mL) and extracted with ethyl acetate (3 × 50 mL). The ethyl acetate layer was washed with brine and dried over MgSO4. The solvent was removed, and the crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to give pure 3 (0.93 g, 74%) as orange red crystals.
Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6006 - 6014
  • 45
  • [ 6374-91-0 ]
  • [ 109-70-6 ]
  • [ 1344698-12-9 ]
YieldReaction ConditionsOperation in experiment
74% 5,7-dibromoisatin 2 (1 g, 3.28 mmol) was taken up in anhydrous DMF (30 mL) and cooled on ice with stirring. Solid K2CO3 (544 mg, 3.94 mmol) was added in one portion, and the dark colored suspension was brought to room temperature and stirred for a further 1 h. 1-Bromo-3-chloropropane (620 mg, 3.94 mmol, 0.387 mL) was added slowly with constant stirring and the reaction mixture was stirred at 80 C for 4-8 h, until the 5,7-dibromoisatin starting material had been consumed (TLC). The reaction mixture was poured into HCl (0.5 M, 50 mL) and extracted with ethyl acetate (3 × 50 mL). The ethyl acetate layer was washed with brine and dried over MgSO4. The solvent was removed, and the crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to give pure 3 (0.93 g, 74%) as orange red crystals, mp 130-132 C. 1H NMR (CDCl3, 500 MHz) δ 2.24-2.39 (m, 2H, H2’), 3.50(t, 1H, J = 6.5 Hz, H3’), 3.67 (t, 1H, J = 6.5 Hz, H3’), 4.31-4.36 (m, 2H, H1’), 7.72 (d, J = 2 Hz, 1H, isatin ArH), 7.91 (d, J = 2.5 Hz, 1H, isatin ArH). HRMS (EI) M+ calcd for C11H8O2N179Br235Cl1, 378.8605; found, 378.8609.
Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6006 - 6014
  • 46
  • [ 6374-91-0 ]
  • [ 187283-17-6 ]
  • tert-butyl [4-((5,7-dibromoisatin-1-yl)methyl)benzyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% General procedure: 5,7-dibromoisatin 2 (1 g, 3.28 mmol) was taken up in anhydrous DMF (30 mL) and cooled on ice with stirring. Solid K2CO3 (544 mg, 3.94 mmol) was added in one portion, and the dark colored suspension was brought to room temperature and stirred for a further 1 h. 1-Bromo-3-chloropropane (620 mg, 3.94 mmol, 0.387 mL) was added slowly with constant stirring and the reaction mixture was stirred at 80 °C for 4-8 h, until the 5,7-dibromoisatin starting material had been consumed (TLC). The reaction mixture was poured into HCl (0.5 M, 50 mL) and extracted with ethyl acetate (3 .x. 50 mL). The ethyl acetate layer was washed with brine and dried over MgSO4. The solvent was removed, and the crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to give pure 3 (0.93 g, 74percent) as orange red crystals.
Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6006 - 6014
  • 47
  • [ 6374-91-0 ]
  • [ 75-52-5 ]
  • [ 1341072-06-7 ]
YieldReaction ConditionsOperation in experiment
77% With 1,4-diaza-bicyclo[2.2.2]octane; at 20℃; for 0.075h;Neat (no solvent); General procedure: To a solution of isatin 1 (1 mmol), nitromethane/nitroethane (3 mmol) was added DABCO (5 mol %). The mixture was stirred at rt this temperature for 1-5 min. The reaction was monitered by TLC. After completion of the reaction, the mixture was extracted with ethyl acetate (3 × 5 mL). The combined organic layers were washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography (ethyl acetate/hexanes: 30:70). All novel compounds were characterized by M.P., NMR, Mass and IR spectral data.
Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5862 - 5864
  • 48
  • [ 6374-91-0 ]
  • [ 587-65-5 ]
  • [ 1228425-56-6 ]
Reference： [1]Medicinal Chemistry Research,2011,vol. 20,p. 615 - 625
[2]Medicinal Chemistry Research,2014,vol. 23,p. 2161 - 2168
  • 49
  • [ 63128-98-3 ]
  • [ 6374-91-0 ]
  • [ 1392495-90-7 ]
YieldReaction ConditionsOperation in experiment
79% With acetic acid; In ethanol; for 0.166667h;Microwave irradiation; General procedure: A suspension mixture of N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazide 2 (2mmol, 0.84g) and appropriate substituted isatin 3a-l (2mmol) and glacial acetic acid (0.02mL) in absolute ethanol was microwave irradiated for 5-15min (depending on substituents on benzene ring of isatins). After irradiating for 1-3min, the suspension mixture became a clear solution. The irradiation was continued in a given time. At the end of reaction process, the precipitate appeared. Upon completion, monitored by TLC, the reaction mixture was cooled to room temperature; the color precipitate was filtered with suction. The crude product was recrystallized from 96% ethanol or mixture of toluene-96% ethanol (2:1 in volume) to afford the title compounds of substituted isatin N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl) thiosemicarbazones 4a-l. The spectral (FT-IR, 1H NMR, 13C NMR and ESI-MS or EI-HRMS) data are in good agreement with their structures.
Reference： [1]Letters in Organic Chemistry,2011,vol. 8,p. 500 - 503
[2]European Journal of Medicinal Chemistry,2016,vol. 123,p. 532 - 543
  • 50
  • [ 6374-91-0 ]
  • [ 107-37-9 ]
  • [ 1309578-02-6 ]
Reference： [1]Letters in Organic Chemistry,2011,vol. 8,p. 352 - 357
  • 51
  • [ 6374-91-0 ]
  • [ 1441-80-1 ]
  • [ 1421695-57-9 ]
YieldReaction ConditionsOperation in experiment
69.8% With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 0.5h; General procedure: For compound 3, arenesulfenyl chloride (5 mmol) was added dropwise to a solution of isatin or isatin derivatives (5 mmol) and triethylamine (5 mmol) in N,N-dimethylformamide (DMF, 5 mL) at room temperature. Stirring was continued for an additional 30 min and then the mixture was poured into ice water (20 mL). The yellow precipitates were collected by filtration and recrystallized from ethanol to give pure 3a-3m.
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 724 - 727
  • 52
  • [ 6374-91-0 ]
  • [ 7669-54-7 ]
  • [ 1421695-56-8 ]
YieldReaction ConditionsOperation in experiment
72.5% With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 0.5h; General procedure: For compound 3, arenesulfenyl chloride (5 mmol) was added dropwise to a solution of isatin or isatin derivatives (5 mmol) and triethylamine (5 mmol) in N,N-dimethylformamide (DMF, 5 mL) at room temperature. Stirring was continued for an additional 30 min and then the mixture was poured into ice water (20 mL). The yellow precipitates were collected by filtration and recrystallized from ethanol to give pure 3a-3m.
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 724 - 727
  • 53
  • [ 83-72-7 ]
  • [ 6374-91-0 ]
  • [ 95-54-5 ]
  • [ 109-77-3 ]
  • [ 1432744-48-3 ]
YieldReaction ConditionsOperation in experiment
91% General procedure: L-Proline (30 mol %)was added to astirred mixture of 2-hy- droxy-1,4 -naphthoquino ne (1) (1mmol)and 1,2-diami ne 2 (1 mmol)in EtOH (10mL)and the mixture refluxedfor 30 min. Then, dialkyl malonate 3 (1 mmol)and the cyclic ketone 4-7 (1 mmol)were added to the mixture,which was refluxedfor the appropriate amount of time (see Table 3). The progress of the reaction was monitored by TLC using EtOAc/ n-hexane (1:3) as eluent. The mixture was cooled to rt and allowed to stand at 25 C for 1h.During this time,crystals of the product were formed and collected by filtration.To obtain the pure product, the crystals were washed with EtOH and Et 2O (2 20 mL) and then dried.
Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2791 - 2794
  • 54
  • [ 683224-24-0 ]
  • [ 6374-91-0 ]
  • [ 1435909-47-9 ]
YieldReaction ConditionsOperation in experiment
51% With methanol; for 10h;Reflux; General procedure: To a solution of the appropriate indoline-2,3-dione 4a-l (1 mmol) in methanol (20 mL) was added 4-phenylpiperazine-1-carbothiohydrazide 3a (0.24 g, 1 mmol). The reaction mixture was stirred at relux for 10 h. The mixture was cooled to room temperature and the precipitate was collected by filtration, dried in air. The crude product was purified by recrystallization from the appropriate solvent to give compounds 5a-l.
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3304 - 3307
  • 55
  • [ 109-06-8 ]
  • [ 6374-91-0 ]
  • [ 1443018-17-4 ]
YieldReaction ConditionsOperation in experiment
75% at 60℃; for 7h;Green chemistry; General procedure: a mixture of isatin (147 mg, 1 mmol) and2,6-dimethylpyridine (321 mg, 3 mmol) was taken in 5 mL polyethyleneglycol-400. The resulting mixture was allowed to stir at 60 C for 5.0 h. Aftercompletion of the reaction, as monitored by TLC, the reaction mixture waspoured into water and extracted with ethyl acetate. The organic layer wasremoved under reduced pressure, and the crude product was purified bycolumn chromatography on silica gel using ethyl acetate:hexane mixture (3:7)as eluent to yield (208 mg 82%) the desired product 3l
Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 3503 - 3506
  • 56
  • [ 6374-91-0 ]
  • [ 14387-17-8 ]
  • 5,7-dibromo-1-(3,5-di-tert-butyl-4-hydroxybenzyl)indoline-2,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 70℃; General procedure: 0.31 g (1.1 mmol) of 3,5-di-tert-butyl-4-hydroxybenzyl acetate 14 and 0.03 mL of triethyl-amine were added to a continuously stirred solution of the isatin derivative 1-13 (1 mmol) in DMF. The reaction was performed at 70, completion of the reaction of the reactants was determined by TLC. After cooling to ambient, the reaction mixture was poured into a brine. The obtained precipitate was filtered off, washed with water, and dried in vacuum (12 mmHg).
Reference： [1]ARKIVOC,2013,vol. 2013,p. 424 - 435
[2]Russian Journal of General Chemistry,2018,vol. 88,p. 57 - 67
    Zh. Obshch. Khim.,2018,vol. 88,p. 61 - 71,11
  • 57
  • [ 6342-56-9 ]
  • [ 6374-91-0 ]
  • (R)-5,7-dibromo-3-hydroxy-3-(3',3'-dimethoxy-2'-oxoprop-1'-yl)-indolin-2-one [ No CAS ]
Reference： [1]European Journal of Organic Chemistry,2013,p. 4780 - 4786
  • 58
  • [ 6342-56-9 ]
  • [ 6374-91-0 ]
  • (S)-5,7-dibromo-3-hydroxy-3-(3',3'-dimethoxy-2'-oxoprop-1'-yl)-indolin-2-one [ No CAS ]
Reference： [1]European Journal of Organic Chemistry,2013,p. 4780 - 4786
  • 59
  • [ 3949-36-8 ]
  • [ 6374-91-0 ]
  • [ 1610544-34-7 ]
Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 237 - 241
  • 60
  • [ 6374-91-0 ]
  • [ 456-42-8 ]
  • [ 1379453-16-3 ]
Reference： [1]ACS Chemical Biology,2014,vol. 9,p. 1015 - 1024
  • 61
  • [ 108-89-4 ]
  • [ 6374-91-0 ]
  • [ 1627617-56-4 ]
Reference： [1]RSC Advances,2014,vol. 4,p. 19789 - 19793
  • 62
  • [ 108-48-5 ]
  • [ 6374-91-0 ]
  • [ 1627617-59-7 ]
Reference： [1]RSC Advances,2014,vol. 4,p. 19789 - 19793
  • 63
  • [ 6374-91-0 ]
  • 1-benzyl-2,4-pyrrolidinedione [ No CAS ]
  • [ 109-77-3 ]
  • [ 1629243-95-3 ]
YieldReaction ConditionsOperation in experiment
91% In ethanol; for 3h;Reflux; General procedure: Spirooxindole Derivatives 4a-r; General ProcedureA mixture of tetramic acid 1a (1 mmol), isatin 2 (1 mmol), andmalononitrile (3; 1 mmol) in EtOH (2 mL) was stirred at reflux for3 h. When the reaction was complete (TLC), the mixture was cooledto r.t. The precipitated product was collected by filtration andwashed successively with H2O and cold EtOH.
Reference： [1]Synthesis,2014,vol. 46,p. 1389 - 1398
  • 64
  • [ 6374-91-0 ]
  • [ 93-08-3 ]
  • C20H13Br2NO3 [ No CAS ]
YieldReaction ConditionsOperation 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:
Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 85,p. 648 - 660
  • 65
  • [ 941-98-0 ]
  • [ 6374-91-0 ]
  • [ 6913-87-7 ]
YieldReaction ConditionsOperation 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:
Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 85,p. 648 - 660
  • 66
  • [ 6374-91-0 ]
  • [ 403-42-9 ]
  • C16H10Br2FNO3 [ No CAS ]
YieldReaction ConditionsOperation 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:
Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 85,p. 648 - 660
  • 67
  • [ 6374-91-0 ]
  • [ 330-94-9 ]
  • (Z)-2-(5,7-dibromo-2-oxoindolin-3-ylidene)-N-(4-fluorophenyl)hydrazinecarbo thioamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With acetic acid; In ethanol; water;Reflux; General procedure: The chemical synthesis route of the target IBT compounds is illustrated in Scheme 1. The IBTs 3 were synthesized by the reaction of isatin 1 and N-phenylhydrazinecarbothioamide 2 in an aqueous solution of ethanol and acetic acid under reflux [22,23]. Generally, equivalent 1 and 2 was dissolved in a solution of acetic acid/water/alcohol solution, and then the mixture was refluxed for approximate 5-6 h. The reaction mixture was subsequently cooled to room temperature and in most cases a yellow or orange solid precipitated out. This precipitate was filtered, washed with water, and then dried to give a crude product. Recrystallization from ethanol gave pure solid in high yields. 4.2.9 (Z)-2-(5,7-Dibromo-2-oxoindolin-3-ylidene)-N-(4-fluorophenyl)hydrazinecarbo thioamide (3-9) Yield 83%; m.p.: 264-265 C; yellow solid; 1H NMR (DMSO-d6, 300 MHz), δ 12.56 (s, 1H, NNH), 11.70 (s, 1H, NH), 10.95 (s, 1H, SCNH), 8.01 (s, 1H, isatin ArH), 7.82 (s, 1H, isatin ArH), 7.61-7.57 (m, 2H, ArH), 7.32-7.26 (m, 2H, ArH); Elemental analysis calculated for C15H9BrN4O5, C: 38.16, H: 1.92, N: 11.87, found C: 38.47, H: 2.12, N: 12.05; ESI-MS m/z: 472, [M - H]-.
Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 419 - 430
  • 68
  • [ 6374-91-0 ]
  • [ 108-94-1 ]
  • [ 109-77-3 ]
  • C20H13Br2N5O [ No CAS ]
Reference： [1]RSC Advances,2015,vol. 5,p. 50421 - 50424
  • 69
  • [ 930-68-7 ]
  • [ 6374-91-0 ]
  • C14H13Br2NO3 [ No CAS ]
Reference： [1]RSC Advances,2015,vol. 5,p. 51581 - 51585

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