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Structure of 162100-83-6

Chemical Structure| 162100-83-6

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Product Details of [ 162100-83-6 ]

CAS No. :162100-83-6
Formula : C10H8ClNO2
M.W : 209.63
SMILES Code : COC(=O)C1=CC2=C(NC=C2)C=C1Cl
MDL No. :MFCD11976069
InChI Key :IGOUVTSYCXABHI-UHFFFAOYSA-N
Pubchem ID :10727132

Safety of [ 162100-83-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280

Computational Chemistry of [ 162100-83-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 9
Fraction Csp3 0.1
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 54.59
TPSA ?

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

42.09 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.03
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

2.53
Log Po/w (WLOGP)?

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

2.61
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.

1.94
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

2.99
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.42

Water Solubility

Log S (ESOL):?

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

-3.08
Solubility 0.175 mg/ml ; 0.000837 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.

-3.06
Solubility 0.182 mg/ml ; 0.00087 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

-3.98
Solubility 0.0218 mg/ml ; 0.000104 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.

-5.78 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

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)

1.56

Application In Synthesis of [ 162100-83-6 ]

* 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 [ 162100-83-6 ]

[ 162100-83-6 ] Synthesis Path-Downstream   1~14

  • 1
  • 5-carboxymethyl-6-chloro-3-thiomethylindole [ No CAS ]
  • [ 162100-83-6 ]
YieldReaction ConditionsOperation in experiment
Isomer b was converted to 6-chloroindole-5-carboxylic acid using the same reaction sequence as described above and was coupled to 4-benzylpiperidine to obtain 6-chloro-5-(4-benzylpiperidinyl)-indole carboxamide as a white solid, MS (M+352).
  • 2
  • [ 162100-83-6 ]
  • [ 256935-86-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; water; In methanol; at 50℃; for 4h; To a solution of <strong>[162100-83-6]6-chloro-1H-indole-5-carboxylic acid methyl ester</strong> (6.0 g, 28.7 mmol) in 200 mL MeOH and 200 mL water was added NaOH (6.0 g) and the mix was heated at 50 C. for 4 h. The solution was cooled, diluted with water and acidified to pH 2-3 and extracted with EtOAc, washed with water and brine. The organic layer was dried with Na2SO4 and concentrated to give the desired product. M+H+(1196).
With sodium hydroxide; LiOH; In tetrahydrofuran; ethyl acetate; EXAMPLE 58C 6-chloro-5-indolecarboxylic acid A solution of Example 58B (1.17 g, approximately 5.6 mmol) in THF (50 mL) was treated with 1M LiOH (56 mL, 56 mmol), heated at 50 C., stirred for 18 hours, treated with 1M NaOH, washed with diethyl ether, acidified with HCl, and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated. The concentrate was purified on silica gel with 50% ethyl acetate/hexanes to provide of 660 mg of the desired product. 1H NMR (DMSO-d6) delta 12.73 (br s, 1H), 11.45 (s, 1H), 8.13 (s, 1H), 7.49 (m, 2H), 6.57 (m, 1H).
Isomer b was converted to 6-chloroindole-5-carboxylic acid using the same reaction sequence as described above and was coupled to 4-benzylpiperidine to obtain 6-chloro-5-(4-benzylpiperidinyl)-indole carboxamide as a white solid, MS (M+352).
  • 3
  • 4-acetylamino-2-chloro-5-trimethylsilanylethynyl-benzoic acid methyl ester [ No CAS ]
  • [ 162100-83-6 ]
YieldReaction ConditionsOperation in experiment
96% With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h;Heating / reflux; To a solution of 4-acetylamino-2-chloro-5-trimethylsilanylethynyl-benzoic acid methyl ester (10 g, 30.9 mmol) in 50 mL THF was added tetrabutylammonium fluoride (14.0 g) and the mix was refluxed for 4 h then extracted with MTBE and washed with water and brine. The organic layer was dried with Na2SO4 and concentrated. The residue was purified by column chromatography using EtOAc and hexane to give the product in 96% yield. M+H+(210).
91 - 92% With tetrabutyl ammonium fluoride; In acetonitrile; at 35 - 80℃; for 7h;Product distribution / selectivity; Example 3 Preparation of -Chloro-S-methoxycarbonyl Indole[0066] A solution of tetrabutylammonium fluoride (TBAF) in acetonitrile was prepared by dissolving 372 kg of TBAF trihydrate in acetonitrile (720 kg) with stirring for at least one hour.[0067] 2-Chloro-4-acetamido-5-(2-trimethylsilylethynyl)-benzoic acid methyl ester (ca.300 kg) was dissolved in acetonitrile (1168 kg) at 20-300C. The TBAF / acetonitrile solution was added to this solution with stirring, while the temperature was maintained at less than 35 0C. The TBAF solution was rinsed in with another portion (49 kg) of acetonitrile.[0068] This mixture was heated to 78-800C for 7 hours or until less than 1% starting material remained as judged by HPLC, and the product accounted for at least 93% of the material by HPLC. The mixture was then vacuum distilled at a temperature not exceeding 35 0C to a volume of about 1200 L. It was then split into two batches, each of which was combined with about 1900 L water at 15-25 0C for one hour to precipitate the product. About half of each batch was spun down in a peeler centrifuge and rinsed with water (198 L); then the other half of each batch was processed similarly. When all of both batches had been processed, the collected off-white to pale brown solids were dried at 35-40 0C to provide a 91-92% yield of material that was 95-97% pure as judged byHPLC.; Example 6; Stage 4C15H18ClNO3Si F. W.323.85 F.W.209.63 SCI-0216435 SCI-0160836[00137] Prior to Campaign S3, tetrabutylammonium fluoride (TBAF) and Stage 4 were charged to the reactor as solids before adding solvent. In Campaign S2, this led to an exothermic reaction between the solids with potential for serious safety consequences. For Campaign S3, TBAF was added successfully as a THF solution. [00138] In Campaign S4, Stage 5 was isolated for the first time as a solid to allow the possibility of registering it as a 'cGMP Starting Material'. The reaction solvent was changed from THF to acetonitrile and the product was isolated by distilling off excess <n="49"/>P A T E N T Attorney Docket: SCI5249WOPCT solvent and adding to a large volume of water. The modified process worked well and yielded Stage 5 product with satisfactory quality.[00139] In Campaign S5, the batch size (Stage 4 input) was increased by a factor of 2.18 and the initial acetonitrile charge was increased from 1.9 to 5.5 volumes to compensate for the very high minimum stirring volume in the reaction vessel. The excess acetonitrile was removed by vacuum distillation prior to quenching the reaction mixture. [00140] The process employed in Campaign S6 was virtually unchanged from S5 apart from a 31 % increase in batch size. This increase permitted a smallqr volume of acetonitrile to be used for the reaction. However, due to volume constraints it was necessary to quench the batch in two halves.[00141] An additional change introduced for both S5 and S6 was the isolation of the product on a centrifuge in place of a vat filter. This generally resulted in better de- liquoring of the wet-cake leading to improved purity and shorter drying times.Comparison of Yield and Purity for Campaigns S3 to S6.[00142] Table One gives a comparison of yield and purity data for Campaigns S4 to S6 inclusive (Stage 5 was not isolated prior to S4).Table One: Stage 5 Yield and Purity Data for Campaigns S4 to S6 <n="50"/>P A T E N T Attorney Docket: SCIS249WOPCT[00143] The data show that physical yield has remained virtually unchanged since Campaign S4. However, Campaigns S5 and S6 showed a dramatic improvement in assay-based yield. The reasons for this are not fully understood. Certainly, the material isolated in S5 and S6 had a much higher assay (>93 % w/w) than the S4 material (84.8 % w/w). This was attributed to isolation on a centrifuge, giving more efficient liquor removal and thus reduced retention of impurities. Similarly, the Stage 4 input for S5 and S6 was purer (>93.8 %w/w) than that used in S4. These facts in themselves do not explain the dramatic increase in assay-based yield. However, it is possible that a purer Stage 4 input may have resulted in a better crystallization and thus a more efficient product recovery.[00144] The Stage 5 product generated in Campaigns S5 and S6 had a higher area % purity than that from S5. Also, as noted above, the % w/w assay was much higher for the S5 and S6 material. Both these observations are consistent with the use of centrifugation in S5 and S6 and the consequent improved efficiency of liquor removal. In S4, there was a marked discrepancy between the product assay (84.8 % w/w) and the HPLC purity (94.7 area %). This is thought to be due to the retention of TBAF-related residues, which are not UV-active. Much better agreement between the assay and area % values was observed in S5 and S6.Process Outline[00145] Below is the process outline of the Stage 5 process employed in Campaign S6. <n="51"/>P A T E N T Attorney Docket: SCI5249WOPCT <n="52"/>P A T E N T Attorney Docket: SCI524...
86% With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 6h;Reflux; Inert atmosphere; Step 2: Preparation of methyl 6-chloro-1H-indole-5-carboxylate. A solution of methyl-2-chloro-4-acetamido-5-(2-trimethylsilylethynyl)-benzoate (1.9 g, 5.9 mmol) in THF (15.0 mL) containing tetrabutyl ammonium fluoride (1.9 g, 6.0 mmol) was heated to reflux for 6 h under nitrogen. The reaction mixture was concentrated to dryness and the residue partitioned between ethyl acetate (25 mL) and water (25 mL). The organic layer was washed with water, dried (Mg504) and concentrated to dryness. The residue was purified by silica gel flash chromatography using 25% ethyl acetate in heptane to afford the title compound as a light brown powder (0.98 g, 86%), m/z 210 (M+H).
83.2 - 92.0% With tetrabutyl ammonium fluoride; In acetonitrile; at 20 - 80℃; for 7h;Product distribution / selectivity; EXAMPLE 3; Preparation of 6-Chloro-5-methoxycarbonyl Indole; A solution of tetrabutylammonium fluoride (TBAF) in acetonitrile was prepared by dissolving 372 kg of TBAF trihydrate in acetonitrile (720 kg) with stirring for at least one hour. 2-Chloro-4-acetamido-5-(2-trimethylsilylethynyl)-benzoic acid methyl ester (ca. 300 kg) was dissolved in acetonitrile (1168 kg) at 20-30 C. The TBAF/acetonitrile solution was added to this solution with stirring, while the temperature was maintained at less than 35 C. The TBAF solution was rinsed in with another portion (49 kg) of acetonitrile. This mixture was heated to 78-80 C. for 7 hours or until less than 1% starting material remained as judged by HPLC, and the product accounted for at least 93% of the material by HPLC. The mixture was then vacuum distilled at a temperature not exceeding 35 C. to a volume of about 1200 L. It was then split into two batches, each of which was combined with about 1900 L water at 15-25 C. for one hour to precipitate the product. About half of each batch was spun down in a peeler centrifuge and rinsed with water (198 L); then the other half of each batch was processed similarly. When all of both batches had been processed, the collected off-white to pale brown solids were dried at 35-40 C. to provide a 91-92% yield of material that was 95-97% pure as judged by HPLC. Laboratory work suggests that this yield may be improved by reducing the volume of acetonitrile present, as by vacuum distillation, prior to the aqueous quench, and by increasing the volume of water used for the quench. This has not been tested on large scale, however. The above examples are simplified descriptions of representative scale-up and pilot plant runs for each of these specific reactions. More detailed descriptions of these examples, including comparison of multiple batches up to pilot plant scale, are presented in the following examples.; EXAMPLE 6 Prior to Campaign S3, tetrabutylammonium fluoride (TBAF) and Stage 4 were charged to the reactor as solids before adding solvent. In Campaign S2, this led to an exothermic reaction between the solids with potential for serious safety consequences. For Campaign S3, TBAF was added successfully as a THF solution. In Campaign S4, Stage 5 was isolated for the first time as a solid to allow the possibility of registering it as a ?cGMP Starting Material?. The reaction solvent was changed from THF to acetonitrile and the product was isolated by distilling off excess solvent and adding to a large volume of water. The modified process worked well and yielded Stage 5 product with satisfactory quality. In Campaign S5, the batch size (Stage 4 input) was increased by a factor of 2.18 and the initial acetonitrile charge was increased from 1.9 to 5.5 volumes to compensate for the very high minimum stirring volume in the reaction vessel. The excess acetonitrile was removed by vacuum distillation prior to quenching the reaction mixture. The process employed in Campaign S6 was virtually unchanged from S5 apart from a 31% increase in batch size. This increase permitted a smaller volume of acetonitrile to be used for the reaction. However, due to volume constraints it was necessary to quench the batch in two halves. An additional change introduced for both S5 and S6 was the isolation of the product on a centrifuge in place of a vat filter. This generally resulted in better de-liquoring of the wet-cake leading to improved purity and shorter drying times. Comparison of Yield and Purity for Campaigns S3 to S6. TABLE ONE Stage 5 Yield and Purity Data for Campaigns S4 to S6 Campaign Stage 5 Campaign Assay- HPLC Physical based Purity Stage 5 Batch Stage 4 Input Stage 5 Output Yield Yield (Area Campaign Number (kg) (kg) (%) (%) %) S4 80011358A, B 99.0 58.2 90.8 83.2 94.7 S5 800125330 202.2 115.4 90.6 89.1 96.4 800125780 210.5 126.6 96.3 S6 80013075A, B 266.2 157.2 92.0 91.4 95.4 80013076A, B 273.4 164.2 97.0 The data show that physical yield has remained virtually unchanged since Campaign S4. However, Campaigns S5 and S6 showed a dramatic improvement in assay-based yield. The reasons for this are not fully understood. Certainly, the material isolated in S5 and S6 had a much higher assay (>93% w/w) than the S4 material (84.8% w/w). This was attributed to isolation on a centrifuge, giving more efficient liquor removal and thus reduced retention of impurities. Similarly, the Stage 4 input for S5 and S6 was purer (>93.8% w/w) than that used in S4. These facts in themselves do not explain the dramatic increase in assay-based yield. However, it is possible that a purer Stage 4 input may have resulted in a better crystallization and thus a more efficient product recovery. The Stage 5 product generated in Campaigns S5 and S6 had a higher area % purity than that from S5. Also, as noted above, the % w/w assay was much higher for the S5 and S6 material. Both these observations are consistent with the use of centrifugation in S5 and S6 and the consequent imp...

  • 4
  • [ 256935-85-0 ]
  • catechol borane [ No CAS ]
  • [ 927-80-0 ]
  • [ 162100-83-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide;tetrakis(triphenylphosphine)palladium (0); In tetrahydrofuran; ethyl acetate; EXAMPLE 58B methyl 6-chloro-5-indolecarboxylate A 50% solution of ethyl ethynyl ether in hexanes (2.1 mL, 10.8 mmol) at 0 C. was slowly treated with 1M catechol borane in THF (9.7 mL, 9.7 mmol), warmed to room temperature, stirred for 2 hours, heated at 70 C. for 2 hours, cooled to room temperature, treated sequentially with Example 58A (1.77 g, 5.69 mmol) in THF (30 mL), tetrakis(triphenylphosphine)-palladium(0) (329 mg, 0.28 mmol), and powdered sodium hydroxide (683 mg, 17.1 mmol), heated to reflux, stirred for 18 hours, cooled to room temperature, treated with 2M HCl (30 mL), stirred for 18 hours, treated with ethyl acetate, washed sequentially with water, 2M Na2CO3, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel to provide the impure desired product which was used in the next step without further purification.
  • 5
  • [ 2457-76-3 ]
  • [ 162100-83-6 ]
  • 6
  • [ 46004-37-9 ]
  • [ 162100-83-6 ]
  • 7
  • [ 256935-85-0 ]
  • [ 162100-83-6 ]
  • 8
  • [ 1036337-13-9 ]
  • [ 162100-83-6 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; In N,N-dimethyl-formamide; at 110℃; for 5h; D. Methyl 6-chloro-1H-indole-5-carboxylate, 23f. A mixture of compound 23e (0.532 mmol, 150 mg) and CuI (0.32 mmol, 60 mg) in DMF (1.5 mL) was heated at 110 C. for 5 h and then cooled to room temperature. The reaction was quenched with water and extracted with EtOAc. The organic layer was concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/hexanes) to give compound 23f.
A mixture of compound 23e (0.532 mmol, 150 mg) and CuI (0.32 mmol, 60 mg) in DMF (1.5 mL) was heated at 110 C. for 5 h and them cooled to room temperature. The reaction was quenched with water and extracted with EtOAc. The organic layer was concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/hexanes) to give compound 23f
A mixture of compound 22m (150 mg, 0.532 mmol) and CuI (60 mg, 0.32 mmol) in DMF (1.5 mL) was heated at 110 C. for 5 h and them cooled to room temperature. The reaction was quenched with water and extracted with EtOAc. The organic layer was concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/hexanes) to give compound 22n.
  • 9
  • 4-acetylamino-5-iodo-2-chloro-benzoic acid methyl ester [ No CAS ]
  • [ 162100-83-6 ]
  • 10
  • [ 162100-83-6 ]
  • [ 75-36-5 ]
  • [ 1380284-62-7 ]
YieldReaction ConditionsOperation in experiment
73% Step 3: Preparation of methyl 3-acetyl-6-chloro-1H-indole-5-carboxylate. To a solution of <strong>[162100-83-6]methyl 6-chloro-1H-indole-5-carboxylate</strong> (0.5 g, 2.4 mmol) in dichloromethane at 0 C, was added drop-wise, a solution of diethyl aluminum chloride (3.6 mL, 1M) and stirred under nitrogen for 45 min. To this mixture, added a solution of acetyl chloride (0.3 g, 3.8 mmol) in dichloromethane (3 mL). The resulting mixture was stirred for 3 h and at room temperature for 30 min. The reaction was quenched by the addition of cold Tris buffer (pH 7.5, 1 mM and added dichloromethane (2×15 mL). The solid that separated was removed by filtration, washed with water and dried to give the title compound (0.44 g, 73%), m/z=252 (M+H).
  • 11
  • [ 162100-83-6 ]
  • [ 1380284-61-6 ]
  • 12
  • [ 162100-83-6 ]
  • [ 1380284-63-8 ]
  • 13
  • [ 162100-83-6 ]
  • [ 1380284-65-0 ]
  • 14
  • [ 162100-83-6 ]
  • [ 1380284-64-9 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 162100-83-6 ]

Chlorides

Chemical Structure| 1245643-61-1

A184633 [1245643-61-1]

Methyl 5-chloro-1H-indole-6-carboxylate

Similarity: 0.97

Chemical Structure| 256935-86-1

A114251 [256935-86-1]

6-Chloro-1H-indole-5-carboxylic acid

Similarity: 0.93

Chemical Structure| 885522-78-1

A264913 [885522-78-1]

Methyl 4-chloro-1H-indole-6-carboxylate

Similarity: 0.92

Chemical Structure| 1082040-57-0

A135103 [1082040-57-0]

Methyl 6-chloro-1H-indole-4-carboxylate

Similarity: 0.88

Chemical Structure| 120100-15-4

A101179 [120100-15-4]

Methyl 3-amino-2-chlorobenzoate

Similarity: 0.87

Esters

Chemical Structure| 1245643-61-1

A184633 [1245643-61-1]

Methyl 5-chloro-1H-indole-6-carboxylate

Similarity: 0.97

Chemical Structure| 885522-78-1

A264913 [885522-78-1]

Methyl 4-chloro-1H-indole-6-carboxylate

Similarity: 0.92

Chemical Structure| 1082040-57-0

A135103 [1082040-57-0]

Methyl 6-chloro-1H-indole-4-carboxylate

Similarity: 0.88

Chemical Structure| 120100-15-4

A101179 [120100-15-4]

Methyl 3-amino-2-chlorobenzoate

Similarity: 0.87

Chemical Structure| 42122-75-8

A234174 [42122-75-8]

Methyl 5-amino-2-chlorobenzoate

Similarity: 0.86

Related Parent Nucleus of
[ 162100-83-6 ]

Indoles

Chemical Structure| 1245643-61-1

A184633 [1245643-61-1]

Methyl 5-chloro-1H-indole-6-carboxylate

Similarity: 0.97

Chemical Structure| 256935-86-1

A114251 [256935-86-1]

6-Chloro-1H-indole-5-carboxylic acid

Similarity: 0.93

Chemical Structure| 885522-78-1

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