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Chemical Structure| 341988-36-1 Chemical Structure| 341988-36-1

Structure of 341988-36-1

Chemical Structure| 341988-36-1

Methyl indoline-6-carboxylate

CAS No.: 341988-36-1

4.5 *For Research Use Only !

Cat. No.: A285956 Purity: 95%

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Product Details of [ 341988-36-1 ]

CAS No. :341988-36-1
Formula : C10H11NO2
M.W : 177.20
SMILES Code : O=C(C1=CC2=C(C=C1)CCN2)OC
MDL No. :MFCD07371629
InChI Key :IVFIWGSRKYSLLR-UHFFFAOYSA-N
Pubchem ID :16244446

Safety of [ 341988-36-1 ]

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

Computational Chemistry of [ 341988-36-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.3
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 52.81
TPSA ?

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

38.33 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.97
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

1.94
Log Po/w (WLOGP)?

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

0.87
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.

1.55
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

2.0
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.67

Water Solubility

Log S (ESOL):?

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

-2.37
Solubility 0.755 mg/ml ; 0.00426 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.

-2.37
Solubility 0.757 mg/ml ; 0.00427 mol/l
Class?

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

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

-3.07
Solubility 0.149 mg/ml ; 0.000843 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.

-6.0 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

1.0
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

0.0 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)

1.61

Application In Synthesis of [ 341988-36-1 ]

* 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 [ 341988-36-1 ]

[ 341988-36-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 50820-65-0 ]
  • [ 341988-36-1 ]
YieldReaction ConditionsOperation in experiment
77% Step 1: A solution of indole-6-carboxylic acid methyl ester (534 mg, 3.05 mmol) in acetic acid (7.5 ml) was cooled to 0° C. Sodium cyanoborohydride (580 mg, 9.2 mmol, 3 equiv.) was added and the mixture stirred at 15° C. for 40 min. A further aliquot of sodium cyanoborohydride (193 mg, 3.05 mmol, 1 equiv.) was added, and the reaction mixture was stirred for 30 min. at room temperature. The solvent was then evaporated, and the residue dissolved in dichloromethane and washed with 1N NaOH. The organic phase was dried with Na2SO4 and evaporated, yielding 2,3-dihydro-1H-indole-6-carboxylic acid methyl ester as a light yellow solid, 494 mg (77percent). This was used as such in the following reaction.
77% A solution of indole-6-carboxylic acid methyl ester (534 mg, 3.05 mmol) in acetic acid (7.5 ml) was cooled to 0° C. Sodium cyanoborohydride (580 mg, 9.2 mmol, 3 equiv.) was added and the mixture stirred at 15° C. for 40 min. A further aliquot of sodium cyanoborohydride (193 mg, 3.05 mmol, 1 equiv.) was added, and the reaction mixture was stirred for 30 min. at room temperature. The solvent was then evaporated, and the residue dissolved in dichloromethane and washed with 1N NaOH. The organic phase was dried with Na2SO4 and evaporated, yielding 2,3-dihydro-1H-indole-6-carboxylic acid methyl ester as a light yellow solid, 494 mg (77percent). This was used as such in the following reaction.
76% With sodium cyanoborohydride; acetic acid; at 20℃; The title compound was prepared according to General Procedure G from methyl indoe~6- carboxylate (200 mg, 1.14 mmo). The crude product was purified b Combifiash silica gel chromatography (0-30percent of EtOAc in hexane), which provided 153 mg (76percent) of the title compound as a colorless solid; NMR (400 MHz, CD ) delta - 7.51 (dd, J = 1,5, 7.6 Hz, 1 H), 7.39 (d, J ~ 15 Hz, 1 H), 7.19 (d, J = 7.6 Hz, 1 H), 3.89 (s, 3 H), 3.67 ( , J = 8,5 Hz, 2 H), 3.12 (t, J *= 8,5 Hz, 2 H). General Procedure 6; Reduction of indole in indolin-e. To the solution of indole (1 eq.) in AcOH (C; 0,5 rnmo) at room temperature was added N38H3CN (3 eq.). The reaction was stirred at the same temperature for 2~4h, The completion of the reaction was monitored by HPLC. Upon completion, H2O was added and the reaction mixture was concentrated to dryness. H2O was added to the crude residue and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCCh, brine and dried over a^SQ^ Filtratio and removal of the solvent provided the desired product, which was used without further purification or purified by Combiflash silica gel chromatography to give the corresponding products.
75% With sodium cyanoborohydride; acetic acid; In dichloromethane; at 0 - 25℃; NaCNBH3 (11.49 g; 0.04 equiv.) was added at 0° C., over a period of 10 minutes, to a solution of methyl 1H-indole-6-carboxylate (8 g; 1 equiv.) in acetic acid (80 ml). The reaction mixture was stirred at 0° C. for 20 minutes and then warmed to room temperature and stirred for 1 hour at room temperature. When the conversion was complete, the acetic acid was distilled off under reduced pressure and the resulting residue was dissolved in dichloromethane. The resulting phases were separated. The organic phase was washed with 1N sodium hydroxide solution and dried over sodium sulfate. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (silica gel, 10-15percent ethyl acetate/hexane). Methyl indoline-6-carboxylate (6 g; 75percent) was obtained in the form of a solid.
73% With sodium cyanoborohydride; acetic acid; at 15℃; for 5h; A solution of methyl lH-indole-6-carboxylate ( 4.80 g, 27.4 mmol ) in acetic acid ( 40 mL ) was cooled to 15 0 C and then treated with sodium cyanoborohydride ( 6.90 g, 0.11 mmol ) added in small portions over 30 min. After 5 h at 15 ° C, the reaction mixture was diluted with a mixture of ice and water ( 200 mL) and carefully adjusted to pH 9 -10 with solid potassium carbonate. The aqueous phase was extracted three times with dichloromethane and the combined organic phase was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residual oil was chromatographed on silica gel ( elution toluene - ethyl acetate 8 : 2 ) to give 3.54 g ( 73 percent yield ) of the title material as yellowish solid. HPLC (Method A): 0.9 min ( tailing ). HRMS (ESI) calcd for Ci0H12NO2 [M+H]+ m/z 178.0863, found 178.0882. 1H NMR (CDC13, 400 MHz) delta ppm: 7.40 (dd, J = 7.6, 1.5 Hz, 1H), 7.25 (d, J = 1.5 Hz, 1H), 7.12 (br. d, J = 7.6 Hz, 1H), 3.85 (s, 3H), 3.59 (t, J = 8.5 Hz, 2H), 3.05 (t, J = 8.5 Hz, 2H).
49% A stirred solution of 2A (1 g, 5.7 mmol) in DCM (20 ml_) and TFA (10 mL) at -200C was treated with Et3SiH (10 mL). The reaction was warmed to RT slowly and stirred thereafter for 17 h. The reaction was quenched with 2 N NaOH until pH 8. The mixture was extracted with DCM (100 mL x 3). The combined organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. Chromatography (20percent EtOAc/hexanes) provided 2B (0.5g, 49percent).
24% With sodium cyanoborohydride; acetic acid; at 30℃; for 16h; To a solution of methyl IH-indole-6-carboxylate (5.0 g, 28.54 mmol) in AcOH (30 mL) wasadded NaBH3CN (5.4 g, 85.62 mmol). The mixture was stirred at 30 °C for 16 h. The reactionwas quenched with sat. aq. NaHCO3 (300 mL) and extracted with EtOAc (100 mL x 3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc = 50 : I to 3 : I) to give the title compound (1.2 g, 24percent) as a whitesolid. ?H NMR (400 MHz, DMSO-d6) oe 7.16 (d, J7.6 Hz, IH), 7.14 (d, J=7.6 Hz, IH), 5.75 (s, IH), 3.78 (s, 3H), 3.52 (t,J 8.4 Hz, 2H), 2.95 (t,J 8.4 Hz, 2H).
With sodium cyanoborohydride; acetic acid; at 0 - 15℃; for 2h; Dissolve methyl indole-6-carboxylate (5.00 g, 28.5 mmol) in acetic acid (50 mL)In a 100 mL single-mouth bottle, sodium cyanoborohydride (8.85 g, 142 mmol) was slowly added at 0 °C.After completion, the reaction was carried out at 15 ° C for 2 hours. After the reaction is complete,The reaction solution was dried to dryness and then purified and evaporated with methylene chloride (200 mL).Extracted with dichloromethane (150 mL × 3),The combined organic phases were dried and concentrated to give the title compound.

  • 2
  • [ 358-23-6 ]
  • [ 341988-36-1 ]
  • 1-Trifluoromethanesulfonyl-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester [ No CAS ]
  • 3
  • [ 341988-36-1 ]
  • 1-Trifluoromethanesulfonyl-2,3-dihydro-1H-indole-6-carboxylic acid [ No CAS ]
  • 4
  • [ 341988-36-1 ]
  • 1-Trifluoromethanesulfonyl-2,3-dihydro-1H-indole-6-carbonyl chloride [ No CAS ]
  • 5
  • [ 341988-36-1 ]
  • [ 152150-17-9 ]
  • 6
  • [ 341988-36-1 ]
  • 2-Diazo-1-(1-trifluoromethanesulfonyl-2,3-dihydro-1H-indol-6-yl)-ethanone [ No CAS ]
  • 7
  • [ 341988-36-1 ]
  • (1-Trifluoromethanesulfonyl-2,3-dihydro-1H-indol-6-yl)-acetic acid ethyl ester [ No CAS ]
  • 8
  • [ 341988-36-1 ]
  • [ 1026402-70-9 ]
  • 9
  • [ 341988-36-1 ]
  • ((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-[2-(1-trifluoromethanesulfonyl-2,3-dihydro-1H-indol-6-yl)-ethyl]-amine [ No CAS ]
  • 10
  • [ 106-93-4 ]
  • [ 341988-36-1 ]
  • [ 341988-29-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In ethyl acetate; Reference Example 7 1-(2-Bromoethyl)-<strong>[341988-36-1]6-methoxycarbonylindoline</strong> To 1,2-dibromoethane (15.7 ml) were added <strong>[341988-36-1]6-methoxycarbonylindoline</strong> (2.41 g) and triethylamine (7.8 ml), and the mixture was stirred at 90° C. for 2 hr. Ethyl acetate (150 ml) was added to the reaction mixture, and the mixture was washed with saturated brine (300 ml) and dried over Na2SO4. Ethyl acetate was evaporated under reduced pressure. The obtained residue was purified by column chromatography to give the title compound (1.71 g). IR v(neat) cm-1; 1713, 1611, 1499.
  • 11
  • [ 22952-32-5 ]
  • [ 341988-36-1 ]
  • [ 928771-94-2 ]
YieldReaction ConditionsOperation in experiment
77% With pyridine; In dichloromethane; at 20℃; Step 2: A solution of <strong>[341988-36-1]2,3-dihydro-1H-indole-6-carboxylic acid methyl ester</strong> (1.34 g, 7.6 mmol) in dichloromethane (66 ml) and pyridine (1.6 ml) was treated with 5-chloro-2-methoxy-benzenesulfonyl chloride (1.83 g, 7.6 mmol, 1 equiv.). The mixture was stirred at room temperature overnight, then diluted with dichloromethane and washed with water. The organic phase was dried with Na2SO4 and evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate gradient), yielding 1-(5-chloro-2-methoxy-benzenesulfonyl)-<strong>[341988-36-1]2,3-dihydro-1H-indole-6-carboxylic acid methyl ester</strong>, 2.2 g (77percent yield). MS (ISP): m/e=382.1 (M+H+.), deltaH (300 MHz; CDCl3) 7.99 (1H, d), 7.93 (1H, s), 7.61 (1H, d), 7.37 (1H, dd), 7.11 (1H, d), 6.77 (1H, d), 4.04 (2H, t), 3.83 (3H, s), 3.56 (3H, s), 3.02 (2H, t).
  • 12
  • [ 2905-27-3 ]
  • [ 341988-36-1 ]
  • [ 1034776-34-5 ]
YieldReaction ConditionsOperation in experiment
92% With pyridine; at 20℃; for 2h; A solution of <strong>[341988-36-1]2,3-dihydro-1H-indole-6-carboxylic acid methyl ester</strong> (0.23 g, 1.30 mmol) in pyridine (0.60 mL) was treated with 3,5-dimethylbenzenesulfonyl chloride (0.30 g, 1.47 mmol) and stirred at room temperature for 2 hours. The mixture was diluted with 1N HCl and extracted with dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulphate and evaporated. The residue was taken up in heptane/ethyl acetate 1:1 and filtered. The filtrate was pure 1-(3,5-dimethyl-benzenesulfonyl)-<strong>[341988-36-1]2,3-dihydro-1H-indole-6-carboxylic acid methyl ester</strong>, 0.41 g (92percent), MS (ISP): m/e=346.3 (M+H).
  • 13
  • [ 341988-36-1 ]
  • [ 1132-17-8 ]
  • [ 1207980-57-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In dichloromethane; at 20℃; for 6.5h;Inert atmosphere; Example 1: Synthesis and analytical data of l-(4-Ethoxy-benzenesulfonyl)-2,3-dihydro- indole-6-carboxylic acid methyl esterl-(4-Ethoxy-benzenesulfonyl)-2,3-dihydro-indole-6-carboxylic acid methyl ester was synthesized starting from commercial available indoline-6-carboxylic acid methylester following the general procedure A using commercial available 4-ethoxy-benzene sulfonylchloride. ESI+, m/z+l=362, found; IH-NMR (CDCl3): delta(ppm)=8.25 (s, IH), 7.8.-7.65 (m, 3H), 7.15 (d, J=2Hz; 1H); 6.90 (d; J=3Hz; 2H), 4,10-3=90 (m, 7H), 2,95 (t, J=2Hz, 2H), 1.40 (t, J=2Hz, 3H) General procedure A: Coupling of sulfonic acid chlorides to indolines0.5 mmol of the Indoline were dissolved in a mixture of 2.5 mL dry dichloromethane and 0.5 mL dry pyridine under a nitrogen atmosphere. 0.6 mmol of the sulfonic acid chloride were added. The mixture was stirred at room temperature in a sealed tube for 6.5 h. Thereafter solvent was evaporated under vacuum. The crude product was purified by preparative HPLC-MS to give the corresponding sulfonamide.
  • 14
  • [ 609-65-4 ]
  • [ 341988-36-1 ]
  • [ 1239952-66-9 ]
YieldReaction ConditionsOperation in experiment
71% General working procedure GWP II-acylation: A solution of the acid chloride B (2 equiv.) was added at room temperature to a solution of the amino acid ester A (1 equiv.) and diisopropylethylamine (1 to 3 equiv.) in dichloromethane. The reaction mixture was stirred for 12 h at room temperature, N,N-dimethylethane-1,2-diamine (1 to 3 equiv.) was added, and stirring was carried out for 1 h at room temperature. The mixture is then washed 3.x. with a 1N HCl solution, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (silica; ethyl acetate/hexane) yielded the desired product.
  • 15
  • [ 55661-08-0 ]
  • [ 341988-36-1 ]
  • [ 1239952-64-7 ]
YieldReaction ConditionsOperation in experiment
99% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25℃; for 12h; General working procedure GWP I-sulfonylation: A solution of the sulfonyl chloride C (1 equiv.) in dichloromethane was added at room temperature to a solution of the amino acid ester A (1.2 equiv.) and diisopropylethylamine (1 to 3 equiv.) in dichloromethane. The reaction mixture was stirred for 12 h at room temperature, then washed 3.x. with a 1N HCl solution, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (silica; ethyl acetate/-hexane) yielded the desired product.
YieldReaction ConditionsOperation in experiment
41 mg With trifluoroacetic acid; In chloroform; at 20℃; for 2h; General procedure: The titled compound (20 mg) as a colorless oil was prepared from the compound [80-2] obtained in the process (2) (992 mg) according to the methods of the processes (1) to (3) of Example 74. 1H-NMR (400 MHz, CDCl3) delta: 6.97 (1H, d, J = 7.3 Hz), 6.63 (1H, d, J = 7.6 Hz), 6.57 (1H, s), 3.68 (3H, s), 3.53 (2H, s), 3.31 (2H, s), 1.29 (6H, s). ESI-MS found: 220 [M+H]+
  • 17
  • [ 341988-36-1 ]
  • methyl 1-acetyl-5-nitroindoline-6-carboxylate [ No CAS ]
  • 18
  • [ 341988-36-1 ]
  • methyl 1-acetyl-5-aminoindoline-6-carboxylate [ No CAS ]
  • 19
  • [ 341988-36-1 ]
  • 1-acetyl-5-[[5-bromo-2-(3-chloro-2-pyridyl)pyrazole-3-carbonyl]amino]-4-chloro-N-isopropylindoline-6-carboxamide [ No CAS ]
  • 20
  • [ 341988-36-1 ]
  • methyl 1-acetyl-5-amino-4-chloroindoline-6-carboxylate [ No CAS ]
  • 21
  • [ 341988-36-1 ]
  • 1-acetyl-5-amino-4-chloroindoline-6-carboxylic acid [ No CAS ]
  • 22
  • [ 341988-36-1 ]
  • 6-acetyl-2-[5-bromo-2-(3-chloro-2-pyridyl)pyrazol-3-yl]-9-chloro-7,8-dihydropyrrolo[2,3g][3,1]benzoxazin-4-one [ No CAS ]
  • 23
  • [ 75-36-5 ]
  • [ 341988-36-1 ]
  • methyl 1-acetylindoline-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine; In dichloromethane; at -30℃;Inert atmosphere; A solution of <strong>[341988-36-1]methyl indoline-6-carboxylate</strong> (42) (50 mg, 0.28 mmol) in dichloromethane (10 mL) was cooled to -30 °C, treated with triethylamine (0.04 mL, 0.3 mmol) followed by dropwise addition of acetyl chloride (0.02 mL, 0.3 mmol), and warmed to RT. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic layers were washed with water, brine solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash-chromatography using ethyl acetate/hexane (3:7) to afford 49 mg 1-acetylindoline-6-carboxylate (43) as a white solid (80percent). 1H NMR (CDCl3, 400 MHz): 8.73 (s, 1H), 7.67 (d, 1H), 7.16 (d, 1H), 4.04 (t, 2H), 3.82 (s, 3H), 3.17 (t, 2H), 2.18 (s, 3H).); MS (electrospray): m/z = 220 [M+1].
  • 24
  • 1-(3-bromo-1-methyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone [ No CAS ]
  • [ 341988-36-1 ]
  • 1-(5-acetyl-1-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)indoline-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% To a solution of <strong>[341988-36-1]methyl indoline-6-carboxylate</strong> (600 mg, 3.40 mmol),1-(3-bromo-l-methyl- 6,7-dihydro-1N-pyrazolo[4,3-clpyridin-5(4H)-yl)ethanone (Intermediate B, 960 mg, 3.74 mmol), 2-dicyclohexylphosphino-2? ,6? -di-i-propoxy- I , 1? -biphenyl (158 mg, 0.34 mmol) andchloro(2-dicyclohexylphosphino-2?,6? -di-i-propoxy- 1,1? -biphenyl) [2-(2- aminoethylphenyl)]palladium(1l), methyl-tert-butylether adduct (277 mg, 0.34 mmol) in dioxane (10 mE) was added e-BuONa (976 mg, 10.20 mmol). The mixture was heated to 120°C for 16 h under a nitrogen atmosphere. After cooling the reaction to room temperature, water (20 mL) was added and the mixture was extracted with EtOAc (20 mE x 2). 1 M HC1(2 mL) was added to aqueous phase and then extracted with EtOAc (20 mL x 2), The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by reverse phase chromatography (acetonitrile 5-35percent / 0.1percent NH4HCO3 in water) to give the title compound (120 mg, 10percent) as a brown solid. ?HNMR (400 MHz, DMSO-d6) oe 7.58 (s, IH), 7.28 (d, J= 7.2 Hz, IH), 7.10 2H), 2.77 - 2.65 (m,2H), 2.08 - 2.06 (m, 3H). LCMS M/Z (M+H) 341.
  • 25
  • 1-(3-bromo-1-methyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone [ No CAS ]
  • [ 341988-36-1 ]
  • methyl 1-(5-acetyl-1-methyl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)indoline-6-carboxylate [ No CAS ]
  • 26
  • [ 341988-36-1 ]
  • indolin-6-ylmethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With lithium aluminium tetrahydride; In tetrahydrofuran; at 23℃; for 3.5h;Inert atmosphere; A solution of <strong>[341988-36-1]methyl indoline-6-carboxylate</strong> ( 0.830 g, 4.68 mmol) in dry tetrahydrofuran ( 20 mL ) was treated at 23 0 C and under nitrogen with lithium aluminum hydride ( 0.23 g, 6.08 mmol) and the resulting mixture was stirred for 3.5 h. The reaction mixture was carefully quenched by successive addition of ethyl acetate ( 1 mL ), water ( 0.2 mL), 15 percent aqueous sodium hydroxide ( 0.2 mL ) and water ( 0.6 mL ). The solid formed was filtered and the filtrate was concentrated under reduced pressure. Chromatography of the residual oil on silica gel ( elution ethyl acetate ) followed by distillation under vacuum ( bulb to bulb distillation, bp 95 - 105 ° C / 0.1 torr, air bath temperature ) gave 0.460 g ( 57 percent yield ) of a clear oil which crystallized to a white solid. HPLC (Method A): 0.132 min. HRMS (ESI) calcd for C9Hi2NO [M+H]+ m/z (0724) 150.0913, found 150.0932. NMR (CDC13, 400 MHz) delta ppm: 7.4 (d, J = 7.4 Hz, 1H), 6.66 (dd, J = 7.4, 1.5 Hz, 1H), 6.63 (br. s, 1H), 4.55 (s, 2H), 3.54 (t, J = 8.4 Hz, 2H), 2.99 (t, J = 8.4 Hz, 2H).
  • 27
  • [ 341988-36-1 ]
  • [ 214614-98-9 ]
  • 28
  • [ 341988-36-1 ]
  • tert-butyl 6-(((6-methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzofuran-4-yl)oxy)methyl)indoline-1-carboxylate [ No CAS ]
  • 29
  • [ 341988-36-1 ]
  • C23H20N4O4S [ No CAS ]
  • 30
  • [ 341988-36-1 ]
  • (6-(((6-Methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzofuran-4-yl)oxy)methyl)indolin-1-yl)(phenyl)methanone [ No CAS ]
  • 31
  • [ 341988-36-1 ]
  • 6-(bromomethyl)-1-((3-(trifluoromethyl)phenyl)sulfonyl)indoline [ No CAS ]
  • 32
  • [ 341988-36-1 ]
  • 6-(((3,5-dichloropyridin-4-yl)oxy)methyl)-1-((3-(trifluoromethyl)phenyl)sulfonyl)indoline trifluoroacetate [ No CAS ]
  • 33
  • [ 341988-36-1 ]
  • 1-((3-(trifluoromethyl)phenyl)sulfonyl)indoline-6-carboxylic acid [ No CAS ]
  • 34
  • [ 341988-36-1 ]
  • N-(2-chloro-6-fluorophenyl)-1-((3-(trifluoromethyl)phenyl)sulfonyl)indoline-6-carboxamide [ No CAS ]
  • 35
  • [ 341988-36-1 ]
  • N-(2-chloro-6-fluorophenyl)-N-methyl-1-((3-(trifluoromethyl)phenyl)sulfonyl)indoline-6-carboxamide [ No CAS ]
 

Historical Records

Technical Information

Categories

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[ 341988-36-1 ]

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