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Chemical Structure| 307951-53-7 Chemical Structure| 307951-53-7

Structure of 307951-53-7

Chemical Structure| 307951-53-7

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

CAS No.: 307951-53-7

4.5 *For Research Use Only !

Cat. No.: A307921 Purity: 95%

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Product Details of [ 307951-53-7 ]

CAS No. :307951-53-7
Formula : C8H7ClN2
M.W : 166.61
SMILES Code : CC1=CC2=C(N1)N=CC=C2Cl
MDL No. :MFCD12924600
InChI Key :OFCAZVVESRXGRC-UHFFFAOYSA-N
Pubchem ID :21081675

Safety of [ 307951-53-7 ]

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

Computational Chemistry of [ 307951-53-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 9
Fraction Csp3 0.12
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 46.07
TPSA ?

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

28.68 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.8
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

2.34
Log Po/w (WLOGP)?

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

2.52
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.

1.9
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

3.12
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.34

Water Solubility

Log S (ESOL):?

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

-2.95
Solubility 0.186 mg/ml ; 0.00112 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.

-2.58
Solubility 0.437 mg/ml ; 0.00262 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

-3.91
Solubility 0.0207 mg/ml ; 0.000124 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.

-5.65 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)

1.41

Application In Synthesis of [ 307951-53-7 ]

* 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 [ 307951-53-7 ]

[ 307951-53-7 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 307951-53-7 ]
  • [ 79-22-1 ]
  • [ 1039122-55-8 ]
  • 3
  • [ 307951-53-7 ]
  • (1,10-phenanthroline)(trifluoromethyl)copper(I) [ No CAS ]
  • [ 73183-34-3 ]
  • [ 1573171-66-0 ]
  • 4
  • [ 307951-53-7 ]
  • [ 73183-34-3 ]
  • [ 1573171-12-6 ]
  • 5
  • [ 307951-53-7 ]
  • N-D 4-chloro-2-methyl-7-azaindole [ No CAS ]
  • 6
  • [ 110-91-8 ]
  • [ 307951-53-7 ]
  • 2-methyl-4-(morpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 170℃; for 3h;Microwave irradiation; Morpholine (1.0 g, 11 mmol) and N,N-diisopropylethylamine (2 mL) wereadded to a mixture of 4-chloro-2-methyl-IH-pyrrolo[2,3-b]pyridine (1.0 g, 6.0 mmol) in 1- methylpyrrolidin-2-one (15 mL). The reaction mixture was heated at 170 C for 3 hoursin a microwave reactor, then diluted with water (30 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo; chromatography on silica gel (Gradient: 0% to 50% ethyl acetate in petroleum ether) provided the product as a white solid. Yield: 1.0 g, 4.6 mmol, 77%. H NMR (400 MHz,DMSO-d6) oe 11.24 (brs, 1H), 7.86 (d, J=5.4 Hz, 1H), 6.38 (d, J=5.5 Hz, 1H), 6.15-6.17 (m, 1 H), 3.74-3.79 (m, 4H), 3.26-3.31 (m, 4H), 2.33 (br s, 3H).
  • 7
  • [ 307951-53-7 ]
  • 3-iodo-2-methyl-4-(morpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • 8
  • [ 307951-53-7 ]
  • 3-iodo-2-methyl-1-[(4-methylphenyl)sulfonyl]-4-(morpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • 9
  • [ 307951-53-7 ]
  • [ 104-94-9 ]
  • N-(4-methoxyphenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; potassium hydroxide; XPhos; In tert-butyl alcohol; at 100℃; for 2h; A stirred mixture of <strong>[307951-53-7]4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine</strong> (20 mg, 0.12 mmol), 4-methoxyaniline (44 mg, 0.36 mmol), palladium(II) acetate (0.54 mg, 0.0024 mmol), 2- dicyclohexylphosphino-2?,4?,6?-triisopropylbiphenyl (2.9 mg, 0.006 mmol) and potassiumhydroxide (40 mg, 0.72 mmol) in t-BuOH (0.5 mL) was heated at 100 C for 2 h, then allowed to cool to ambient temperature. The resulting mixture was added to water (1 mL) and extracted with EtOAc (3 x 2 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of CH2C12:MeOH - 100:0 to 90:10, to give the title compound. MS: m/z = 254.1 (M +1). ?H NMR (400 MHz, CD3OD) oe 7.69 (d, 1H, J= 5.8 Hz), 7.21 (m, 2H), 6.93 (m, 2H), 6.44 (d, 1H, J 5.8 Hz), 6.16 (q, 1H, J 1.0 Hz), 3.80 (s, 3H), 2.39 (d, 3H, J= 1.0 Hz).
  • 10
  • [ 52462-29-0 ]
  • [ 307951-53-7 ]
  • [Ru(η6-p-cymene)(2-methyl-4-chloro-7-azaindole)Cl2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20℃; for 3h; General procedure: [Ru(mu-Cl)(eta6-p-cym)Cl]2 (0.1 mmol, 61.2 mg) was dissolved in methanol (5 mL) and left toreact with two molar equivalents of the corresponding naza. The reaction mixture was stirredat ambient temperature for 20 min (reactions with 5Braza and 5Faza), 2 h (reactions with aza,3Iaza and 3Claza) or 3 h (reactions with 2Me4Claza, 3Cl5Braza and 3I5Braza), until the yellow(for 2, 4 and 5), or light (for 8) or dark (for 1, 3, 6 and 7) orange product was formed. Theproducts (Fig 1) were isolated by filtration, washed with methanol (2 × 2 mL) and diethyl ether(3 × 5 mL) and dried under the infrared lamp (40C, 4 h). The yields were 60-80%.
  • 11
  • potassium tetraiodoplatinate [ No CAS ]
  • [ 307951-53-7 ]
  • cis-[PtI2(2Me4Claza)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20℃; General procedure: The platinum(II) diiodido complexes 1±8 (Fig 1) were prepared using a slight modification ofthe recently reported protocol [21]. Briefly, 0.5 mmol (207.5 mg) of K2[PtCl4] was dissolved in5 mL of deionized water at 60 C and an excess of KI (415.0 mg; 2.5 mmol) was added to the red solution, which turned dark red over 10 min of stirring at 60 C. After cooling to ambienttemperature, 1.0 mmol of naza (118.1 mg for aza, 152.6 mg for 3Claza and 4Claza, 197.0 mg for3Braza, 4Braza 5Braza, 244.0 mg for 3Iaza and 166.6 mg for 2Me4Claza; Fig 1) dissolved in 5mL of methanol was poured in. The mixture was stirred overnight at ambient temperature andthe obtained yellow solid was removed by filtration and washed with deionized water (3 × 5mL), methanol (3 × 2 mL) and diethyl ether (3 × 5 mL). The products (yields ~90%) weredried under vacuum and stored in desiccator over silica gel.
  • 12
  • [ 307951-53-7 ]
  • (S)-tert-butyl (1-(2-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate [ No CAS ]
  • (S)-tert-butyl (1-(2-cyano-4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II); caesium carbonate; In tetrahydrofuran; water; at 65℃; for 5h;Inert atmosphere; A mixture of (S)-tert-butyl (2,4-dimethyl-l-(2-methyl-4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)phenoxy) pentan-2-yl)carbamate (prepared using the procedure described in Example 285) (0.070 g, 0.156 mmol), 4-chloro-2- methylpyrimidine (0.02 g, 0.156 mmol), and tripotassium phosphate (2M Solution) (0.5 mL, 1.00 mmol) in THF (2 mL) was purged with nitrogen fori 5 min. XPhos 2nd generation precatalyst (0.037 g, 0.047 mmol) was added and the mixture purged for a further 5 min. The reaction mixture was then stirred at 75 C for 2.5 h. The reaction mixture was cooled to room temperature and diluted with THF (15 mL) and filtered through diatomaceous earth (Celite). The bed was washed with excess of THF. The filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate and pet ether) to afford (S)-tert- butyl (2,4-dimethyl-l -(2-methyl-4-(2-methylpyrimidin-4-yl)phenoxy)pentan-2- yl)carbamate (0.018 g, 0.036 mmol, 23% yield) as a yellow oil. LCMS (ESI) m/e 414.4 [(M+H) +, calcd for C24H36N3O3, 414.26]; LC/MS retention time (method A2); to = 2.30 min.
  • 13
  • [ 307951-53-7 ]
  • (S)-tert-butyl (1-(2-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate [ No CAS ]
  • (S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)benzonitrile [ No CAS ]
  • 14
  • [ 307951-53-7 ]
  • (S)-tert-butyl (2,4-dimethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy)pentan-2-yl)carbamate [ No CAS ]
  • (S)-tert-butyl (2,4-dimethyl-1-(4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(trifluoromethyl)phenoxy)pentan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II); caesium carbonate; In tetrahydrofuran; water; at 65℃; for 4h;Inert atmosphere; A mixture of 4-chloro-2-methyl-lH-pyrrolo[2,3-Z>]pyridine (0.028 g, 0.141 mmol), (S)-tert-bu y (2,4-dimethyl-l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-2-(trifluoromethyl)phenoxy)pentan-2-yl)carbamate (prepared as described in Example 215, Parts A and B) (0.071 g, 0.141 mmol), and CS2CO3 (0.069 g, 0.212 mmol) in THF (2 mL) and water (0.667 mL) was purged with nitrogen for 15 min. XPhos 2nd generation precatalyst (0.017 g, 0.021 mmol) was added and nitrogen gas was bubbled through reaction mixture for 5 min and stirred at 65 C for 4 h. The reaction mixture was cooled to room temperature and diluted with THF (10 mL) and filtered through diatomaceous earth (Celite). The bed was washed with excess THF. The filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate and pet ether) to afford (S)-tert- butyl (2,4-dimethyl-l-(4-(2-methyl-lH-pyrrolo[2,3- )]pyridin-4-yl)-2- (trifluoromethyl)phenoxy)pentan-2-yl)carbamate (0.032 g, 0.062 mmol, 44% yield) as a pale yellow oil. LCMS (ESI) m/e 506.2 [(M+H)+, calcd for C27H36F3N3O3, 506.26]; LC/MS retention time (Method Al); fa = 2.80 min.
  • 15
  • [ 307951-53-7 ]
  • (S)-tert-butyl (2,4-dimethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy)pentan-2-yl)carbamate [ No CAS ]
  • (S)-2,4-dimethyl-1-(4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(trifluoromethyl)phenoxy)pentan-2-amine [ No CAS ]
  • 16
  • 4-chloro-1-((4-ethylphenyl)sulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • [ 307951-53-7 ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydroxide; In methanol; at 70℃; for 5h; To a solution of 4-chloro-l-((4-ethylphenyl)sulfonyl)-2-methyl-lH- pyrrolo [2,3 -b] pyridine (0.2 g, 0.585 mmol) in MeOH (4 mL) was added 5M NaOH solution (0.585 mL, 2.93 mmol) at room temperature. The whole mixture was heated at 70 C for 5 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with ethyl acetate (15 mL) and water (10 mL). The organic layer was re-extracted with ethyl acetate (2 x 10 mL). The combined organics were dried and concentrated to afford 4-chloro-2- methyl-lH-pyrrolo[2,3-Z>]pyridine (0.1 g, 0.504 mmol, 86% yield) as a pale yellow solid. LCMS (ESI) m/e 167.2 [(M+H)+, calcd for C8H8C1N2 , 167.03]; LC/MS retention time (Method Al); fa = 1.82 min.
  • 17
  • [ 307951-53-7 ]
  • [ 74-88-4 ]
  • 4-chloro-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydroxide; In N,N-dimethyl-formamide; at -10℃; for 4h; At -10 C, to a solution of 4- chloro-2-methyl- 1 H-pyrrolo [2,3 -bjpyridine (338 mg, 2.03 minol) in N,N-dimethylfonnamide (10 mL) was added sodium hydroxide (240 mg, 6.00 minol). Then lodomethane (284 mg, 2.00 minol) was added and the resultingminxture was stirred for 4 h at -10 C. When the reaction was done, the reactionminxture was deluted by DCM (100 mL) and the resultingminxture was washed with water (30 mL x 3). The organic phase was washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in petroleum ether (0% to 10% gradient) to yield 4-chloro-1,2-dimethyl-1H- pyrrolo[2,3-bjpyridine as yellow solid (300 mg, 82%). MS: m/z = 181.0 [M+Hj.
  • 18
  • [ 307951-53-7 ]
  • tert-butyl (3R,5S)-1-(1,2-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-5-methylpiperidin-3-ylcarbamate [ No CAS ]
  • 19
  • [ 307951-53-7 ]
  • (2S,6R)-4-(1,2-dimethyl-1h-pyrrolo[2,3-b]pyridin-4-yl)-2,6-dimethylmorpholine [ No CAS ]
  • 20
  • [ 307951-53-7 ]
  • [ 98-59-9 ]
  • 4-chloro-2-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% To a 250 mL round bottom flask was added NaH (60% dispersion in mineral oil, 1.39 g, 34.8 mmol) as a solid. The flask was evacuated and backfilled with N2. DMF (25 mL) was added and the round bottom flask was placed into an ice/water bath and cooled to 3 ?C. A solution of 4-chloro-2-methyl-lH- pyrrolo[2,3-?]pyridine (4.07 g, 24.4 mmol) in DMF (34 mL) was then added slowly (over 45 minutes) via addition funnel and was stirred for 45 min. /?-Toluenesulfonyl chloride (5.75 g, 29.9 mmol) was dissolved into DMF (33 mL) and the resulting solution was added dropwise over 20 minutes. Reaction progress was monitored by LCMS analysis. NOTE: attempts to add additional quantities of TsCl did not push reaction conversion further. The reaction was poured slowly onto 500 mL ice water while stirring vigorously, which caused a precipitate to form. Next was added 1 M NaOH (35 mL) and the reaction was stirred for 1 h. The solids were collected by suction filtration. The solids were crushed to a fine powder and dried under vacuum for 1 day using high vacuum (100 mTorr) to afford the title compound (7.82 g, 95%) as a tan powder. MS (ESI): mass calcd. for C15H13CIN2O2S, 320.0; m/z found, 321.0 [M+H]<+>.<1>H NMR (500 MHz, CDCh): ? 8.25 (d, J = 5.3 Hz, 1H), 8.06 - 7.96 (m, 2H), 7.30 - 7.23 (m, 2H), 7.13 (d, J = 5.3 Hz, 1H), 6.42 - 6.37 (m, 1H), 2.74 (s, 3H), 2.36 (s, 3H).
  • 21
  • [ 307951-53-7 ]
  • 2-tert-butoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-[2-(trifluoromethyl)-1-piperidyl]pyridine [ No CAS ]
  • 4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-6-[2-(trifluoromethyl)-1-piperidyl]-1H-pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
3% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 2h; 2-tert-Butoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-6-[2- (trifluoromethyl)-1 -piperidyl]pyridine (1 10 mg, 0.26 mmol), 4-chloro-2-methyl- 1 H-pyrrolo[2,3-b]pyridine (95 mg, 0.57 mmol), K2CO3 (89 mg, 0.64 mmol) and PdCl2(dppf) (14 mg, 0.02) were taken up in 1 ,4-dioxane and water and the mixture was stirred at 90 C for 2h. When cooled to rt EtOAc was added and the mixture filtered. The organic layer was separated, dried over MgSO4 and concentrated. The resulting residue was dissolved in DCM, TFA (0.1 1 ml, 1 .54 mmol) was added, the mixture stirred at rt for 30 min, concentrated and purified by preparative HPLC to give the product as a solid (3.4 mg, 3 %). 1H NMR (500 MHz, METHANOL-^) delta ppm 1 .62 - 1 .70 (m, 1 H), 1 .76 - 1 .94 (m, 4 H), 2.07 - 2.16 (m, 1 H), 2.51 (d, 3 H), 3.19 - 3.28 (m, 1 H), 3.85 - 4.06 (m, 1 H), 5.37 (br d, 1 H), 6.32 (d, 1 H), 6.36 (d, 1 H), 6.39 - 6.47 (m, 1 H), 7.17 (d, 1 H), 8.06 - 8.27 (m, 1 H). MS ES+ m/z 377 [M+H]+.
 

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Related Functional Groups of
[ 307951-53-7 ]

Chlorides

Chemical Structure| 1000340-38-4

A205026 [1000340-38-4]

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Related Parent Nucleus of
[ 307951-53-7 ]

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