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Chemical Structure| 171919-36-1 Chemical Structure| 171919-36-1

Structure of 171919-36-1

Chemical Structure| 171919-36-1

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Product Details of [ 171919-36-1 ]

CAS No. :171919-36-1
Formula : C9H8N2O
M.W : 160.17
SMILES Code : O=CC1=CN(C)C2=NC=CC=C21
MDL No. :MFCD11054209
InChI Key :IZPRBMBNUDLUMD-UHFFFAOYSA-N
Pubchem ID :10441960

Safety of [ 171919-36-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 171919-36-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 9
Fraction Csp3 0.11
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 46.38
TPSA ?

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

34.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.51
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

0.73
Log Po/w (WLOGP)?

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

1.39
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.

0.67
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

1.56
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.17

Water Solubility

Log S (ESOL):?

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

-1.78
Solubility 2.65 mg/ml ; 0.0165 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.04
Solubility 14.6 mg/ml ; 0.0909 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

-2.41
Solubility 0.623 mg/ml ; 0.00389 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.

-6.76 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

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)

1.33

Application In Synthesis of [ 171919-36-1 ]

* 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 [ 171919-36-1 ]

[ 171919-36-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 27257-15-4 ]
  • [ 68-12-2 ]
  • [ 171919-36-1 ]
YieldReaction ConditionsOperation in experiment
74% b) 1-Methyl-lH-pyrrolo [2, 3-b] pyridine-3-carbaldehyde; POC13 (1.2 g, 7.9 mmol) was added dropwise with stirring to 10 mL of DMF at 0C. After stirring 10 min a solution of 1-methyl-lH-pyrrolo [2, 3-b] pyridine (0.95 g, 7. 2 mmol) in 5 mL of DMF was added during 1 min. The reaction mixture was stirred for lh at 0C and a further 30 min at 60C. It was poured into water which was made alkaline with NaHC03 (aq) and extracted 3 times with EtOAc. The combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product (0.85 g, 74%) was sufficiently pure to be used in the subsequent step below. 'H NMR (300 MHz, CDC13) No. 9. 97 (s, 1H), 8.55 (m, 1H), 8.44 (m, 1H), 7.84 (s, 1H), 7.27 (m, 1H), 3.97 (s, 3H).
9. 7-[2-(4-CYCLOBUTYLPIPERAZIN-l-YL)-2-OXOETHYL]-9-METHYL- 6,7,8,9-TETRAHYDRO-5H-PYRIDO[4',3':4,5]PYRROLO[2,3-B]PYRIDINE (SCHEME 7); Compound 9; Step 1. 1 -Methyl- 1 H-pyrro Io [2,3 -b]pyridine-3-carbaldehyde; <n="63"/>POCl3 (1.48 mL, 9.65 mmol) is added dropwise to a 0 0C solution of DMF (5 mL). The mixture is stirred 0.5 h at 0 0C. In a separate flask, 1 -methyl- IH- pyrrolo[2,3-b]pyridine (Journal of the American Chemical Society (2005) 127(22):8050-57; 1.04 g, 7.87 mmol) is dissolved in DMF (10 mL) and added dropwise to the first solution at 0 0C. The mixture is allowed to warm to rt and stirred overnight. The mixture is diluted with water (100 mL) and basified with IO N NaOH. The mixture is extracted with DCM (3 x 50 mL). The combined organic extracts are washed with water (3 x 100 mL) and brine (100 mL), dried over Na2SO4, and evaporated to yield the title compound. MS (+VE) m/z 161.12 (M+ +1).
General procedure: POCl3 (5.87 ml, 63.0 mmol) was added dropwise to DMF (45 ml) at 0 C, and the mixture was stirred for 20 min at same temperature. A solution of 6-fluoro-1-methylindole (6.71 g, 45.0 mmol) in DMF (45 ml) was added slowly to the mixture at 0 C. After being stirred at room temperature for 1.5 h, the reaction mixture was poured into ice, and the resulting mixture was neutralized with 1 N NaOH and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, and concentrated to dryness. The residue was purified by column chromatography on silica gel with EtOAc as eluent to give the title compound (4.18 g, 52%) as a colorless solid.
  • 2
  • [ 171919-36-1 ]
  • [ 171919-37-2 ]
  • 4
  • [ 171919-36-1 ]
  • 1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid benzotriazol-1-yl ester [ No CAS ]
  • 5
  • [ 171919-36-1 ]
  • 1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid ((1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide [ No CAS ]
  • 6
  • [ 171919-36-1 ]
  • 1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid ((1R,3R,5S)-9-methyl-9-aza-bicyclo[3.3.1]non-3-yl)-amide [ No CAS ]
  • 7
  • [ 27257-15-4 ]
  • [ 171919-36-1 ]
YieldReaction ConditionsOperation in experiment
83% With sodium hydrogencarbonate; trichlorophosphate; In ethyl acetate; N,N-dimethyl-formamide; (Step 2) Synthesis of 1-methyl-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde Phosphoryl chloride (5.15 ml, 55.3 mmol) was added dropwise to DMF (70 ml) under stirring at 0ØC. After the reaction mixture was stirred at 0ØC for 10 minutes, a solution of 1-methyl-1H-pyrrolo(2,3-b)pyridine (4.87 g, 36.8 mmol) in DMF (5 ml) was added dropwise at the same temperature. After completion of the dropwise addition, the reaction mixture was stirred at 0ØC for 4 hours and at 60ØC for 3.5 hours. The reaction mixture was poured in ice water - a saturated aqueous solution of sodium bicarbonate to neutralize the mixture therewith, followed by extraction with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from ethyl acetate eluate fractions, 1-methyl-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde (4.87 g, 83%) was obtained as a yellow solid. 1H-NMR (CDCl3) delta: 3.98 (s, 3H), 7.28 (dd, J=7.8,4.7Hz, 1H), 7.85 (s, 1H), 8.44 (d, J=4.7Hz, 1H), 8.55 (d, J=7.8Hz, 1H), 9.97 (s, 1H). MS (ESI) m/z 160 (M+-H).
47% b) 1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde According to the procedure of Preparation 40 (b), except substituting 1-methyl-1H-pyrrolo[2,3-b]pyridine (0.7 g, 5.3 mmole) for the 1,3-dimethylindole, the title compound (0.4 g, 47%) was prepared as a white solid: MS (ES) m/e 161 (M + H)+.
  • 8
  • [ 860297-22-9 ]
  • [ 171919-36-1 ]
  • C24H24FN5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; c) (1S, 35)-N-(6-Fluoro-4-methylquinolin-2-yl)-lV-l (1-methyl-lH-pyrrolo [2, 3-b] pyridin- 3-yl) methyl] cyclopentane-1, 3-diamine; (1S, 3S)-N-(6-Fluoro-4-methylquinolin-2-yl)cyclopentane-1, 3-diamine (76 mg, 0.29 mmol ; see Ex 6b) and 1-methyl-lH-pyrrolo [2, 3-b] pyridine-3-carbaldehyde (47 mg, 29 mmo; from step b above) were dissolved in 2 mL of methanol and allowed to react overnight. Sodium borohydride (50 mg, 1.3 mmol) was added and the reaction mixture was stirred for 15 min after which 5 mL of 2M HC1 was added and after an additional 5 min the mixture was made alkaline by addition of 2M NaOH. The mixture was extracted three times with EtOAc and the combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product was chromatographed on a pre-packed SiO2-column (Isolute, 5 g) eluted with DCM: MeOH: Et3N 100: 5: 1 to give 78 mg (65%) of the title compound after freeze-drying from dioxane. 'H NMR (400 MHz, CDCl3) 8 8.30 (m, 1H), 7.93 (m, 1H), 7.60 (dd, 1H), 7.32 (dd, 1H), 7.24 (m, 1H), 7.07, (s, 1H), 7.01 (dd, 1H), 6.48 (s, 1H), 4.93 (m, 1H), 4.42 (m, 1H), 3.89 (s, 2H), 3.81 (s, 3H), 3.37 (m, 1H), 2.45 (s, 3H), 2.35-2. 20 (m, 2H), 2.15-1. 95 (m, 2H), 1.80 (m, 1H), 1.50 (m, 1H). 3C NMR (101 MHz, CDC13) additional signals due to C-F coupling 8 159.9, 157.5, 156.9, 148.9, 145.6, 145.3, 143.8, 129.0, 128.9, 128.0, 127.9, 124.7, 124.6, 120.7, 119.4, 119.1, 116. 0, 113. 0, 112. 7,108. 5,108. 3,58. 3,52. 6,44. 2,41. 6,33. 3,32. 7,31. 9,19. 7. LC-MS [M+H] +404. 2
  • 9
  • [ 171919-36-1 ]
  • [ 335033-16-4 ]
YieldReaction ConditionsOperation in experiment
45% c) 1-Methyl-3-(methylaminomethyl)-1H-pyrrolo[2,3-b]pyridine According to the procedure of Preparation 40 (c), except substituting 1-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (0.4 g, 2.5 mmole) for the 1,3-dimethyl-1H-indole-2-carboxaldehyde, the title compound (0.2 g, 45%) was prepared as a yellow oil: MS (ES) m/e 176 (M + H)+.
  • 10
  • [ 75-52-5 ]
  • [ 171919-36-1 ]
  • [ 1094709-34-8 ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; at 70℃; Step 2. l-Methyl-3-[(E)-2-nitrovinyl]-lH-pyrrolo[2,3-b]pyridine; To a solution of l-methyl-lH-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1.18 g, 7.34 mmol) in nitromethane (20 mL) is added NH4OAc (200 mg, 2.59 mmol). The mixture is stirred overnight at 70 0C. The solution is cooled to rt and concentrated under reduced pressure. The residue is dissolved in EtOAc (50 mL) and extracted with saturated aqueous NaHCO3 (2 x 50 mL). The organic extract is dried over Na2SO4, and evaporated to yield the title compound. MS (+VE) m/z 204.18 (M+ +1).
  • 11
  • [ 4649-09-6 ]
  • [ 616-38-6 ]
  • [ 171919-36-1 ]
  • 12
  • [ 171919-36-1 ]
  • [ 1099-45-2 ]
  • [ 1220533-82-3 ]
  • 14
  • [ 542-92-7 ]
  • [ 171919-36-1 ]
  • [ 1289648-29-8 ]
  • 15
  • [ 353525-11-8 ]
  • [ 171919-36-1 ]
  • [ 441716-30-9 ]
YieldReaction ConditionsOperation in experiment
General procedure: A mixture of 6-fluoro-1-methylindole-3-carbaldehyde (13a) (500 mg, 2.82 mmol) and methyl 4-amino-3-hydroxyphenylacetate (11a) (767 mg, 4.23 mmol) in EtOH (15 ml) was stirred for 22 h, and iodobenzene diacetate (1.09 g, 3.38 mmol) was added portionwise to the mixture. After being stirred for 1 h, the mixture was concentrated, and the residue was purified column chromatography with n-hexane-AcOEt (1:1, v/v) as eluent to give methyl [2-(6-fluoro-1-methyl-3-indolyl)-6-benzoxazolyl]acetate (889 mg, 93%) as a brown solid.
  • 16
  • [ 171919-36-1 ]
  • [ 441715-88-4 ]
  • 17
  • [ 171919-36-1 ]
  • [ 441715-87-3 ]
  • 18
  • [ 171919-36-1 ]
  • [ 441712-69-2 ]
  • 19
  • [ 104-94-9 ]
  • [ 171919-36-1 ]
  • [ 1355338-02-1 ]
  • 20
  • [ 104-94-9 ]
  • [ 171919-36-1 ]
  • C16H15N3O [ No CAS ]
  • 21
  • [ 110-18-9 ]
  • [ 27257-15-4 ]
  • [ 171919-36-1 ]
YieldReaction ConditionsOperation in experiment
60% With water; iodine; oxygen; sodium carbonate; In 1,4-dioxane; at 100℃; under 760.051 Torr; for 36h;Schlenk technique; Sealed tube; General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 muL, 0.5 mmol, 2.5 equiv), Na2CO3 (42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H2O (100 muL). Then I2 (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O2. The reaction mixture was stirred at 100 C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products.
  • 22
  • [ 21777-85-5 ]
  • [ 171919-36-1 ]
  • (1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)(1-(phenylethynyl)cyclopropyl)methanol [ No CAS ]
  • 23
  • [ 171919-36-1 ]
  • [ 197376-41-3 ]
  • [ 1449006-72-7 ]
YieldReaction ConditionsOperation in experiment
89% General procedure: Titanium tetrachloride (1.90 g, 10 mmol) was slowly added to100 mL of anhydrous THF at 0 C, followed by addition of 5 mmol of the aldehyde (1) and stirred for 10 min, then ethyl 2-(3-bromopyridin-2-yl)acetate (2) (1.47 g, 6 mmol) was added. Subsequently, a solution of pyridine (3.16 g, 40 mmol) in 25 mL of anhydrous THF was added dropwise during a period of 30-60 min at 0 C. The reaction mixture was then stirred for 1 h at room temperature and refluxed for 24 h. After that the mixture was poured on to crashed ice and extracted with ethyl acetate (4 30 mL). The combined extracts were successively washed with brine, saturated sodium hydrogen carbonate and brine, and then dried over anhydrous MgSO4. The organic phase was filtrated and the solvent was removed in vacuo, the residue was purified by column chromatography (silica gel) using PE/EA (5:1) / DCM/MeOH (50:1) to provide 3.
  • 24
  • [ 27257-15-4 ]
  • [ 67-68-5 ]
  • [ 171919-36-1 ]
  • 25
  • tert-butyl 6-benzyloxy-7-methoxy-1-[(1-phenyltetrazol-5-yl)sulfonylmethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate [ No CAS ]
  • [ 171919-36-1 ]
  • [ 76-05-1 ]
  • 6-(benzyloxy)-7-methoxy-1-[(E)-2-{1-methyl-1H-pyrrolo[1,2,3-b]pyridin-3-yl}ethenyl]-1,2,3,4-tetrahydroisoquinoline trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.5% To a solution of tert-butyl 6-benzyloxy-7-methoxy-1-[(1-phenyltetrazol-5-yl)sulfonylmethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate [118 mg (0.2 mmol)] in THF (5 ml) with <strong>[171919-36-1]1-methylpyrrolo[2,3-b]pyridine-3-carbaldehyde</strong> [96 mg (0.6 mmol)] was added at -38 C. 1M LiN(TMSi)2 [600 ul (0.6 mmol)]. The reaction was stirred at -38 C. for 60 min and then at room temperature for 30 min longer. The reaction was quenched with sat NH4Cl (10 ml), extracted with EtOAc (20 ml), dried (MgSO4) and the solvent removed. The residue was treated with 2 ml of 4NHCl in dioxane for 1 h, rotary evaporated to dryness and chromatographed via reverse phase chromatography. Yield=3 mg (3.5%) as TFA salt via prep chrom. MS (m/z): 426 [M+H]
  • 26
  • [ 536-74-3 ]
  • [ 171919-36-1 ]
  • 1-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-phenylprop-2-yn-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% General procedure: To the ice-cold solution of aldehyde in THF was added, the solution of alkylmagnesium halide or alkyllithium in THF (1.3 eq., at 0 C). The reaction was stirred at 0 C for 1 h, diluted with saturated aq. NH4Cl (10 mL) and ethyl acetate (10 mL). Aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (10 mL), and dried over Na2SO4. Evaporation of the solvent and purification of the crude mixture by column chromatography (9:1, hexane: EtOAc) gave the corresponding bisindolylmethane derivatives (BIM) up to 92% yields along with the by-product aldehyde.
  • 27
  • [ 54655-07-1 ]
  • [ 171919-36-1 ]
  • 1-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-(trimethylsilyl)prop-2-yn-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In tetrahydrofuran; at 0℃; for 1h; General procedure: To the ice-cold solution of aldehyde in THF was added, the solution of alkylmagnesium halide or alkyllithium in THF (1.3 eq., at 0 C). The reaction was stirred at 0 C for 1 h, diluted with saturated aq. NH4Cl (10 mL) and ethyl acetate (10 mL). Aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (10 mL), and dried over Na2SO4. Evaporation of the solvent and purification of the crude mixture by column chromatography (9:1, hexane: EtOAc) gave the corresponding bisindolylmethane derivatives (BIM) up to 92% yields along with the by-product aldehyde.
  • 28
  • C13H16NO(1+) [ No CAS ]
  • [ 171919-36-1 ]
  • C22H22N3O(1+) [ No CAS ]
  • 29
  • [ 591-50-4 ]
  • [ 171919-36-1 ]
  • [ 1198277-81-4 ]
  • 30
  • [ 50-00-0 ]
  • [ 27257-15-4 ]
  • [ 171919-36-1 ]
  • 31
  • [ 171919-36-1 ]
  • C11H8N2O2 [ No CAS ]
  • 32
  • [ 171919-36-1 ]
  • 1-methyl-3-(phenylethynyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • 33
  • [ 558-13-4 ]
  • [ 171919-36-1 ]
  • C10H8Br2N2 [ No CAS ]
  • 34
  • [ 171919-36-1 ]
  • methyl 3-formyl-1-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylate [ No CAS ]
  • 35
  • [ 124-38-9 ]
  • [ 171919-36-1 ]
  • C10H8N2O3 [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 171919-36-1 ]

Aldehydes

Chemical Structure| 728034-12-6

A188666 [728034-12-6]

1H-Pyrrolo[2,3-b]pyridine-4-carbaldehyde

Similarity: 0.86

Chemical Structure| 757978-33-9

A210999 [757978-33-9]

5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Similarity: 0.84

Chemical Structure| 918515-16-9

A106165 [918515-16-9]

4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Similarity: 0.81

Chemical Structure| 900514-07-0

A194920 [900514-07-0]

3-Iodo-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Similarity: 0.78

Chemical Structure| 144657-66-9

A216004 [144657-66-9]

tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

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Related Parent Nucleus of
[ 171919-36-1 ]

Other Aromatic Heterocycles

Chemical Structure| 171919-37-2

A137483 [171919-37-2]

1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

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Chemical Structure| 728034-12-6

A188666 [728034-12-6]

1H-Pyrrolo[2,3-b]pyridine-4-carbaldehyde

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Chemical Structure| 757978-33-9

A210999 [757978-33-9]

5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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Chemical Structure| 156270-06-3

A163883 [156270-06-3]

1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid

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Chemical Structure| 27257-15-4

A304720 [27257-15-4]

1-Methyl-1H-pyrrolo[2,3-b]pyridine

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