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Chemical Structure| 6326-79-0

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Product Details of [ 6326-79-0 ]

CAS No. :6326-79-0
Formula : C8H4BrNO2
M.W : 226.03
SMILES Code : C1=C(Br)C=CC2=C1NC(=O)C2=O
MDL No. :MFCD01631138
InChI Key :HVPQMLZLINVIHW-UHFFFAOYSA-N
Pubchem ID :95716

Safety of [ 6326-79-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Computational Chemistry of [ 6326-79-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
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 49.86
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

46.17 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.14
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.33
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.01
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.91
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.19
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.32

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.45
Solubility 0.803 mg/ml ; 0.00355 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.9
Solubility 2.84 mg/ml ; 0.0126 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.64
Solubility 0.0521 mg/ml ; 0.000231 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.73 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.7

Application In Synthesis of [ 6326-79-0 ]

* 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 [ 6326-79-0 ]

[ 6326-79-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 6326-79-0 ]
  • [ 77-78-1 ]
  • [ 667463-64-1 ]
YieldReaction ConditionsOperation in experiment
85% With sodium carbonate; In acetone; at 60℃; for 20h; To a solution of 3a (150 mg, 0.66 mmol) in dry acetone (30 mL) was added Na2CO3 (anh. ) (1.0 g) and dimethylsulfate (0.8 mL) under Ar and the reaction mixture was heated at 60 C for 20 h. Then, the mixture was filtered and the filtrate was carefully evaporated using a high vacuum pump (under 40 C). The solid residue was submitted to flash chromatography with CH2C12 to afford lla (140 mg, 0.58 mmol, 85%) (see Scheme 2 in Fig. 2B).
63% The 1.15g (5mmol) 6- bromo-isatin was dissolved in 10mL DMF,1.03 g (7.5 mmol) of potassium carbonate was added with stirring.Then, 0.804 g (6.25 mmol) of dimethyl sulfate was added dropwise, and the mixture was reacted at room temperature for 4 hours, and the mixture was poured into 100 mL of ice water.The extract was extracted with ethyl acetate (60 mL×3), and the organic layer was evaporated.After concentrated to dryness, it was purified by silica gel column chromatography ( petroleum ether: ethyl acetate = 20:3)0.753 g of a red solid was obtained in a yield of 63%.
With sodium hydride; In N,N-dimethyl-formamide;Inert atmosphere; General procedure: A mixture of 2-bromoaniline or 3-bromoaniline (110 mmol, 18.9 g), chloral hydrate (118.8 mmol,19.6 g), anhydrous sodium sulfate (880 mmol, 125 g), and hydroxylamine hydrochloride (347.6mmol, 24.2 g) in water (700 mL) was heated under reflux for 25 min to form a yellow precipitate. 50mL of ethanol was added after that and left to boil for another 4 min before filtration. The resultedisonitrosoacetanilide was then heated with sulfuric acid (150 mL) at 70 C for about 10 min thenpoured into ice water to form an orange precipitate. When using 3-bromoaniline, an extra step ofseparation is required by solving the resulted mixture in 0.25 M NaOH (1 L), filtering it, then addingacetic acid (100 mL) to afford 4-bromoistain as a precipitate. 6-Bromoistin can be then obtained whenlowering the pH of the solution to 1 by hydrochloric acid 37%.All substituted bromo-isatins were methylated by stirring (22 mmol, 4.97 g) with sodiumhydride (2 mmol, 0.968 g) and dimethylsulfate (23.1 mmol, 2.19 mL) in dried DMF (50 mL) undernitrogen atmosphere. The resulting mixture was poured after 2 h in ice water (100 mL) to form anorange precipitate.The methylated bromo-isatins (2 mmol, 0.480 g) were treated after that with oxindole (2 mmol,0.226 g) in a 100:1 mixture of glacial acetic acid and hydrochloric acid 37% (12 mL) in reflux for about 3 h. Then, they were poured in ice water (50 mL) to afford 5-, 6- and 7-bromomeisoindigo. While 4'-, 5'-, 6'- and 7'-bromomeisoindigo were obtained by reacting unmethylated bromo-isatins(2 mmol, 0.452 g) with 1-methyloxindole (2 mmol, 0.294 g) in the same conditions. The resultedprecipitates were washed with water, ethanol (2 x 10 mL), and diethylether (2 10 mL) then dried.
  • 2
  • [ 6326-79-0 ]
  • [ 74-88-4 ]
  • [ 667463-64-1 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate; In acetonitrile; at 60℃; for 1.5h; To a solution of 6-bromoindoline-2,3-dione (0.504 g,2.23 mmol)in acetonitrile (11 mL)was added K2C03 (1.23 g,8.92 mmol)then iodomethane (0.278 mL,4.46 mmol). The reactionmixture was heated at 60 oc for 1.5 h. After cooling to room temperature,water (30 mL)wasadded and the mixture was extracted with DCM (30 mL x 3). The combined organic layers were washed with brine (30 mL),dried over anhydrous Na2S04 and then concentrated in underreduced pressure to give the title compound (0.506 g,95%)that required no further purification.1HNMR(400MHz,CDCl3)87.46(dd,J=7.9,l.OHz,1H),7.32-7.28(m,1H),7.08(d,J=1.5 Hz,1H),3.25 (d,J = 0.6 Hz,3H).
65% With potassium carbonate; In acetonitrile; at 60℃; for 0.75h; To R4 (500 mg, 2.21 mmol) in acetonitrile (15 mL) is added Mel (0.303 mL, 4.87 mmol) and K2CO3 (1.2 g, 8.68 mmol) and the reaction mixture stirred at 60 C for 45 min DCM and water is added and the aqueous layer extracted twice with DCM, the combined organic layers are washed with brine, dried and concentrated. Yield 65%. m/z 240/242 [M+H]+, rt 0.49 min, LC-MS Method b.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; Step 1: Synthesis of Intermediate 1-12.1 To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; To R7 (25.0 g, I I I mmol) in acetonitrile (750 mL) is added Mel (15 mL, 24ltnmol) and KzC03(60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture isfiltered and concentrated. Water and ethyl acetate are added to the residue. The organic layer isextracted twice with water, dried over MgS04 and concentrated. Yield 56%, mlz 240/242 [M+H]+,rt 0.48 min, LC-MS Method XOOl_ 004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; Step 1: Synthesis of Intermediate 1-5.1To RiO (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 mL, 241 mmol) and K2C03(60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture isfiltered and concentrated. Water and ethyl acetate are added to the residue. The organic layer isextracted twice with water, is dried over MgSO4 and concentrated. Yield 56%, m/z 240/242[M+H]+, rt 0.48 mi LC-MS Method X001 004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; To R7 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; Synthesis of 1-Methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one (R7) Step 1: Synthesis of Intermediate I-4.1 [0293] To R12 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; To R12 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.
With potassium carbonate; In acetonitrile; at 60℃; for 0.666667h; To a solution of 6-bromorsatin (CASNo. 6326-79-0, 4 52 g, 20 0 mmol) in acetonrtrile (150 mL) was added potassium carbonate (11 1 g, 80 mmol) followed by iodomethane (2 75 mL, 44 0 mmol) The reactron was then placed at 60 C and stirred for 40 minutes The reaction was then cooled to room temperature, tittered and concentrated to 10% of the original volume The reaction was then diluted with dichloromethane, water and brine The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate filtered and concentrated to provide 6-bromo-1-methyl-1 H-iotandole-2,3- dione as an orange solid without the need for further punfication The beta-bromo-1-methyl- 1 H-iotandole-2,3-diotaone (1 0 g, 4 2 mmol) was then treated with hydrazine hydrate (7 0 mL, 225 mmol) The reaction was heated to 130 C and stirred for 80 minutes, at which time the reaction was placed at room temperature and cooled by the addition of ice Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 2%) to afford 6-bromo- 1-methyl-1 ,3-diotahydro-mdol-2-one, MS (ES+) m/z 225 9 (IvH-H)*
General procedure: Isatins I (3.0 mmol) was dissolved in anhydrous DMF (15 mL), and the resultant solution was cooled to 0 C (ice bath), whereupon sodium hydride (60% dispersion in mineral oil, 140mg, 3.5 mmol, 1.17 equiv) was added in one portion and stirred for 5 minutes. Iodomethane (497 mg, 3.5 mmol, 1.17 equiv) or benzyl bromide (564.3 mg, 3.3 mmol, 1.1 equiv) was added and the reaction was stirred at 0 C for 30min. The reaction was monitored by TLC until I was fully consumed. The reaction mixture was then poured into saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic portions were washed with water and brine, dried (MgSO4), filtered, and concentrated to give N-methyl isatins and N-benzyl isatins II (90%-100% yield).
With sodium hydride; In N,N-dimethyl-formamide; at 0℃; General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

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  • 3
  • [ 6326-79-0 ]
  • MeX, X = halide [ No CAS ]
  • [ 667463-64-1 ]
  • 4
  • [ 6326-79-0 ]
  • [ 34557-54-5 ]
  • [ 667463-64-1 ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate; In acetonitrile; at 60℃; for 0.75h; To R4 (500 mg, 2.21 mmol) in acetonitrile (15 mL) is added Met (0.303 mL, 4.87 mmol) and K2CO3 (1.2 g, 8.68 mmol) and the reaction mixture stirred at 60 C. for 45 min. DCM and water is added and the aqueous layer extracted twice with DCM, the combined organic layers are washed with brine, dried and concentrated. Yield 65%. m/z 240/242 [M+H]+, rt 0.49 min, LC-MS Method b.
  • 5
  • [ 6326-79-0 ]
  • methylating agent [ No CAS ]
  • [ 667463-64-1 ]
YieldReaction ConditionsOperation in experiment
56% With potassium carbonate; In acetonitrile; at 60℃; for 2h; To R10 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Met (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, is dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.
  • 6
  • [ 6326-79-0 ]
  • CH3-X, X=halide [ No CAS ]
  • [ 667463-64-1 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; In N,N-dimethyl-formamide; at 65℃; General procedure: To a solution of 6-bromoindoline-2,3-dione (7a) or 6-bromo-7-methylindoline-2,3-dione (7b) (3.94mmol) in dry N, N-dimethylformamide (5mL) was added K2CO3 (1.3g, 9.44mmol) and alkyl halides (4.72mmol) at 0C. The reaction mixture was stirred at 65C for 1-2h. After completion of reaction as determined by TLC analysis, the reaction solution was poured into water (25mL) and extracted with CH2Cl2 (3×100mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate 10:1-3:1) to afford 8a-8c. 6-Bromo-1-methylindoline-2, 3-dione (8a) Yield 90%; 1H NMR (400 MHz, CDCl3) delta 3.26 (s, 3H), 7.09 (s, 1H), 7.29-7.31 (m, 1H), 7.47 (d, 1H, J = 8.0 Hz). 13C NMR (100 MHz, CDCl3) delta 26.4, 113.7, 116.1, 126.3, 127.1, 133.7, 152.2, 158.1, 182.1.
  • 7
  • [ 6326-79-0 ]
  • [ 1131-18-6 ]
  • [ 50607-30-2 ]
  • 6-bromo-3'-methyl-1'-phenyl-6',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b][1,6]naphthyridine]-2,5'(1'H)-dione [ No CAS ]
  • 8
  • [ 6326-79-0 ]
  • [ 112253-70-0 ]
YieldReaction ConditionsOperation in experiment
81% With ammonium hydroxide; dihydrogen peroxide; In dimethyl sulfoxide; at 20 - 30℃; for 4h;Sealed tube; General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25%, 421 mg, 3.0 mmol) and H2O2 (30%, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30% NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89% yield).
 

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 6326-79-0 ]

Bromides

Chemical Structure| 87-48-9

A194051 [87-48-9]

5-Bromoindoline-2,3-dione

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5-Bromo-7-ethylindoline-2,3-dione

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A394784 [2058-72-2]

5-Bromo-1-methylindoline-2,3-dione

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Chemical Structure| 17826-05-0

A252185 [17826-05-0]

5,6-Dibromoindoline-2,3-dione

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Chemical Structure| 20780-72-7

A267730 [20780-72-7]

4-Bromoindoline-2,3-dione

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Amides

Chemical Structure| 87-48-9

A194051 [87-48-9]

5-Bromoindoline-2,3-dione

Similarity: 0.99

Chemical Structure| 34921-60-3

A263853 [34921-60-3]

5-Bromo-7-ethylindoline-2,3-dione

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A394784 [2058-72-2]

5-Bromo-1-methylindoline-2,3-dione

Similarity: 0.95

Chemical Structure| 17826-05-0

A252185 [17826-05-0]

5,6-Dibromoindoline-2,3-dione

Similarity: 0.89

Chemical Structure| 20780-72-7

A267730 [20780-72-7]

4-Bromoindoline-2,3-dione

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Ketones

Chemical Structure| 87-48-9

A194051 [87-48-9]

5-Bromoindoline-2,3-dione

Similarity: 0.99

Chemical Structure| 34921-60-3

A263853 [34921-60-3]

5-Bromo-7-ethylindoline-2,3-dione

Similarity: 0.96

Chemical Structure| 2058-72-2

A394784 [2058-72-2]

5-Bromo-1-methylindoline-2,3-dione

Similarity: 0.95

Chemical Structure| 17826-05-0

A252185 [17826-05-0]

5,6-Dibromoindoline-2,3-dione

Similarity: 0.89

Chemical Structure| 20780-72-7

A267730 [20780-72-7]

4-Bromoindoline-2,3-dione

Similarity: 0.86

Related Parent Nucleus of
[ 6326-79-0 ]

Indolines

Chemical Structure| 87-48-9

A194051 [87-48-9]

5-Bromoindoline-2,3-dione

Similarity: 0.99

Chemical Structure| 34921-60-3

A263853 [34921-60-3]

5-Bromo-7-ethylindoline-2,3-dione

Similarity: 0.96

Chemical Structure| 2058-72-2

A394784 [2058-72-2]

5-Bromo-1-methylindoline-2,3-dione

Similarity: 0.95

Chemical Structure| 17826-05-0

A252185 [17826-05-0]

5,6-Dibromoindoline-2,3-dione

Similarity: 0.89

Chemical Structure| 20780-72-7

A267730 [20780-72-7]

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Similarity: 0.86