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Chemical Structure| 372120-55-3 Chemical Structure| 372120-55-3

Structure of 372120-55-3

Chemical Structure| 372120-55-3

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Product Details of [ 372120-55-3 ]

CAS No. :372120-55-3
Formula : C8H4BrF3O
M.W : 253.02
SMILES Code : O=CC1=CC=C(C(F)(F)F)C(Br)=C1
MDL No. :MFCD13185384
Boiling Point : No data available
InChI Key :MWYYNBYTVFKXSD-UHFFFAOYSA-N
Pubchem ID :11482172

Safety of [ 372120-55-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 372120-55-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 44.53
TPSA ?

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

17.07 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.82
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

2.96
Log Po/w (WLOGP)?

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

4.43
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.

3.23
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

3.68
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.22

Water Solubility

Log S (ESOL):?

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

-3.48
Solubility 0.0832 mg/ml ; 0.000329 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.

-2.98
Solubility 0.264 mg/ml ; 0.00104 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

-4.09
Solubility 0.0206 mg/ml ; 0.0000815 mol/l
Class?

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

Moderately 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.

-5.74 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<0.0
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)

1.55

Application In Synthesis of [ 372120-55-3 ]

* 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 [ 372120-55-3 ]

[ 372120-55-3 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 17115-51-4 ]
  • [ 5220-49-5 ]
  • [ 372120-55-3 ]
  • 9-(3-bromo-4-trifluoromethyl-phenyl)-3a-hydroxy-1,1-dioxo-1,2,3,3a,4,5,6,7,9,9a-decahydro-1λ6-thieno[3,2-<i>b</i>]quinolin-8-one [ No CAS ]
  • 2
  • [ 372120-51-9 ]
  • [ 372120-55-3 ]
  • 3
  • [ 455-24-3 ]
  • [ 372120-55-3 ]
  • 4
  • [ 116965-16-3 ]
  • [ 372120-55-3 ]
  • 5
  • [ 372120-55-3 ]
  • [ 714951-30-1 ]
  • 6
  • [ 372120-55-3 ]
  • 9-(3-bromo-4-trifluoromethyl-phenyl)-1,1-dioxo-1,2,3,4,5,6,7,9-octahydro-1λ6-thieno[3,2-<i>b</i>]quinolin-8-one [ No CAS ]
  • 7
  • [ 372119-86-3 ]
  • [ 372120-55-3 ]
  • 8
  • 3-bromo-4-(trifluoromethyl)benzoyl chloride [ No CAS ]
  • [ 372120-55-3 ]
  • 9
  • [ 372120-54-2 ]
  • [ 372120-55-3 ]
YieldReaction ConditionsOperation in experiment
With manganese dioxide; In chloroform; EXAMPLE 63B 3-bromo-4-(trifluoromethyl)benzaldehyde The product from Example 63A in chloroform (100 mL) was treated with manganese dioxide (1.1 g, 12.6 mmol) and stirred overnight. The mixture was filtered and the filtrate was concentrated. The residue was chromatographed on silica gel eluding with 15% ethyl acetate/hexanes to rovide the title compound (0.28 g). 1H NMR (CDCl3) delta 7.9 (m, 2H), 8.2 (s, 1H), 10.02 (s, 1H).
  • 10
  • [ 867-13-0 ]
  • [ 372120-55-3 ]
  • [ 1427690-53-6 ]
YieldReaction ConditionsOperation in experiment
98% To a solution of a 60% dispersion of NaH in mineral oil (0.31 g, 7.75 mmol) in DME (2 mL) at - 30 C was added a solution of ethyl 2-phosphonoacetate (1.46 mL, 7.29 mmol) in DME (13 mL), and the mixture was stirred at this temperature for 30 min. To this solution was added a solution of <strong>[372120-55-3]3-bromo-4-(trifluoromethyl)benzaldehyde</strong> (44) (1.68 g, 6.63 mmol) in DME (3 mL), and the reaction was stirred at -30 C for 1.5 h and then poured into water (50 mL) and extracted with ethyl acetate. The combined organic layers were washed with an aqueous saturated NH4C1 solution and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to give a crude product that was purified by column chromatography (150 mL Si02, ethyl acetate :hexanes 5:95) to give 45 (2.1 188 g, 98%) as a colorless crystalline solid: 1H NMR (400 MHz, CDC13) ? 7.84 (s, 1H), 7.69 (d, J= 8.0, 1H), 7.59 (d, J= 16.0, 1H), 7.52 (d, J= 8.0, 1H), 6.50, (d, J= 16.0, 1H), 4.27 (q, J= 7.2, 2H), 1.34 (t, J= 7.2, 3H); 13C NMR (100.6 MHz, CDC13) ? 165.9, 141.0, 139.2, 133.8, 131.4, 130.7, 130.4, 128.3, 128.2, 128.1, 128.1, 126.4, 123.9, 122.2, 121.2, 120.6, 120.5, 60.9, 14.2.
  • 13
  • [ 372120-55-3 ]
  • 1-(3-bromo-4-trifluoromethylpheny)ethanone [ No CAS ]
  • 14
  • [ 917-64-6 ]
  • [ 372120-55-3 ]
  • 1-(3-bromo-4-trifluoromethylphenyl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; diethyl ether; for 0.5h;Cooling with ice; Step 1 (0506) To a mixture of <strong>[372120-55-3]3-bromo-4-trifluoromethylbenzaldehyde</strong> (2 g) and tetrahydrofuran (36 mL) was added methylmagnesium iodide (2 mol/L diethylether solution, 4.35 mL) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. The mixture was diluted with ammonium chloride aqueous solution and ethyl acetate. The ethyl acetate layer was washed with brine, and concentrated under reduced pressure to give 1-(3-bromo-4-trifluoromethylphenyl-ethanol.
  • 15
  • [ 110-91-8 ]
  • [ 372120-55-3 ]
  • 3-morpholino-4-(trifluoromethyl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 85℃;Inert atmosphere; A 250-mL round-bottom flask was charged with <strong>[372120-55-3]3-bromo-4-(trifluoromethyl)benzaldehyde</strong> (3.00 g, 1 1.9 mmol, 1.00 equiv), 2,2'-bis(diphenylphosphino)- l, l'-binaphthyl (1.1 1 g, 1.78 mmol, 0.15 equiv), cesium carbonate (1 1.6 g, 35.6 mmol, 3.00 equiv), tris(dibenzylideneacetone)dipalladium (0.545 g, 0.600 mmol, 0.05 equiv), toluene (60 mL), and morpholine (1.55 g, 17.8 mmol, 1.50 equiv) under nitrogen. The resulting solution was stirred overnight at 85 C and quenched with water (80 mL). The resulting solution was extracted with EtOAc (2 x 150 mL) and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column to provide 2.00 g (65% yield) of 3-morpholino-4- (trifluoromethyl)benzaldehyde as a yellow solid. LCMS (ESI, m/z): 260 [M+H]+.
  • 16
  • [ 372120-55-3 ]
  • 5-((8-(3-acetamido-1H-pyrazole-1-carbonyl)-1,8-diazaspiro[4.5]decan-1-yl)methyl)-2-(trifluoromethyl)benzamide [ No CAS ]
  • 17
  • [ 372120-55-3 ]
  • 2-(4-(5-((4-(3-(methylsulfonamido)-1H-pyrazole-1-carbonyl)piperazin-1-yl)methyl)-2-(trifluoromethyl)phenyl)piperidin-1-yl)acetic acid [ No CAS ]
  • 18
  • [ 372120-55-3 ]
  • tert-butyl 1-(3-(methoxycarbonyl)-4-(trifluoromethyl)benzyl)-1,8-diazaspiro[4.5]decane-8-carboxylate [ No CAS ]
  • 19
  • [ 372120-55-3 ]
  • 5-((8-(tert-butoxycarbonyl)-1,8-diazaspiro[4.5]decan-1-yl)methyl)-2-(trifluoromethyl)benzoic acid [ No CAS ]
  • 20
  • [ 372120-55-3 ]
  • tert-butyl 1-(3-carbamoyl-4-(trifluoromethyl)benzyl)-1,8-diazaspiro[4.5]decane-8-carboxylate [ No CAS ]
  • 21
  • [ 372120-55-3 ]
  • 5-(1,8-diazaspiro[4.5]decan-1-ylmethyl)-2-(trifluoromethyl)benzamide [ No CAS ]
  • 22
  • [ 372120-55-3 ]
  • 5-(1,8-diazaspiro[4.5]decan-1-ylmethyl)-2-(trifluoromethyl)benzoic acid [ No CAS ]
  • 23
  • [ 372120-55-3 ]
  • tert-butyl 4-(5-((4-(3-(methylsulfonamido)-1H-pyrazole-1-carbonyl)piperazin-1-yl)methyl)-2-(trifluoromethyl)phenyl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
  • 24
  • [ 372120-55-3 ]
  • tert-butyl 4-(5-((4-(3-(methylsulfonamido)-1H-pyrazole-1-carbonyl)piperazin-1-yl)methyl)-2-(trifluoromethyl)phenyl)piperidine-1-carboxylate [ No CAS ]
  • 25
  • [ 372120-55-3 ]
  • N-(1-(4-(3-(piperidin-4-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carbonyl)-1H-pyrazol-3-yl)methanesulfonamide trifluoroacetate [ No CAS ]
  • 26
  • [ 372120-55-3 ]
  • tert-butyl 2-(4-(5-((4-(3-(methylsulfonamido)-1H-pyrazole-1-carbonyl)piperazin-1-yl)methyl)-2-(trifluoromethyl)phenyl)piperidin-1-yl)acetate [ No CAS ]
  • 27
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 372120-55-3 ]
  • methyl 5-formyl-2-(trifluoromethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; at 100℃; A 250-mL round-bottom flask was charged with 3-bromo-4- (trifluoromethyl)benzaldehyde (3.00 g, 11.9 mmol, 1.00 equiv), MeOH (50 mL), 1,1?- bis(diphenylphosphino)ferrocenepalladiumdichloride (870 mg, 1.19 mmol, 0.10 equiv), and triethylamine (3.61 g, 35.7 mmol, 3.00 equiv). Carbon monoxide (10 atm) was introduced. The resulting solution was stirred overnight at 100 C and quenched with water (50 mL). The resulting solution was extracted with EtOAc (2 x 80 mL) and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column to provide 2.20 g (80% yield) of methyl 5- formyl-2-(trifluoromethyl)benzoate as an off-white semi-solid. ?H NIVIR (400 MHz, Chloroform-cl) oe 10.1 (s, 1H), 8.31 (s, 1H), 8.12 - 8.15 (m, 1H), 7.97 (d, J= 8.0 Hz, 1H), 4.00 (s, 3H).
80% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; at 100℃; Example 178: 1,1,1,3,3,3-Hexafluoropropan-2-yl 1-(3-carbamoyl-4-(trifluoromethyl)benzyl)- 1,8-diazaspiro[4.5]decane-8-carboxylate Step 1: Synthesis of methyl 5-formyl-2-(trifluoromethyl)benzoate A flask was charged with <strong>[372120-55-3]3-bromo-4-(trifluoromethyl)benzaldehyde</strong> (3.00 g, 11.9 mmol, 1.00 equiv), MeOH (50 mL), 1,1'-bis(diphenylphosphino)ferrocenepalladiumdichloride (870 mg, 1.19 mmol, 0.10 equiv), and TEA (3.61 g, 35.7 mmol, 3.00 equiv). Carbon monoxide (10 atm) was introduced, and the reaction was stirred overnight at 100 C before quenching with water (50 mL). The resulting solution was extracted with EtOAc (2 x 80 mL) and the organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was chromatographed on a silica gel column with EtOAc/petroleum ether (8/92) to provide 2.2 g (80% yield) of methyl 5-formyl-2-(trifluoromethyl)benzoate as an off-white semi-solid.1H NMR (400 MHz, Chloroform-d) ^ 10.1 (s, 1H), 8.31 (s, 1H), 8.12- 8.15 (m, 1H), 7.97 (d, J = 8.0 Hz, 1H), 4.00 (s, 3H).
73% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; at 65℃; under 11400.8 Torr;Autoclave; A 100-mL autoclave was charged with <strong>[372120-55-3]3-bromo-4-(trifluoromethyl)benzaldehyde</strong> (3.00g, 11.9 mmol, 1.00 equiv), 1,1?-bis(diphenylphosphino)ferrocenepalladiumdichloride (0.869 g,1.19 mmol, 0.10 equiv), triethylamine (3.61 g, 35.7 mmol, 3.00 equiv), and methanol (50 mL). The contents of the autoclave were placed under an atmosphere of carbon monoxide (15 atm). The resulting solution was stirred overnight at 65 C and quenched with water (50 mL). The reaction mixture was extracted with dichloromethane (3 x 50 mL) and the organic layers were combined, washed with brine (1 x 100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column to provide 2.00 g (73% yield) of methyl 5-formyl-2-(trifluoromethyl)benzoate. ?H NMR (300 MHz, Chloroform-cl) oe 10.4 (s, 1H), 8.31 (s, 1H), 8.14 (d, J 8.1 Hz, 1H), 7.97 (d, J 8.1 Hz, 1H), 4.01 (s, 3H).
  • 28
  • [ 375853-82-0 ]
  • [ 372120-55-3 ]
  • tert-butyl 4-(5-formyl-2-(trifluoromethyl)phenyl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere; A 50-mL round-bottom flask was charged with 3-bromo-4- (trifluoromethyl)benzaldehyde (1 .00 g, 3.95 mmol, 1.00 equiv), tert-butyl 4-(tetramethyl- 1,3,2- dioxaborolan-2-yl)- 1,2,3 ,6-tetrahydropyridine- 1 -carboxylate (1.84 g, 5.95 mmol, 1.50 equiv), tetrakis(triphenylphosphine)palladium (230 mg, 0.198 mmol, 0.05 equiv), potassium carbonate (1.64 g, 11.9 mmol, 3.00 equiv), 1,4-dioxane (10 mL), and water (2 mL) under nitrogen. The resulting solution was stirred overnight at 80 C and quenched with water (10 mL). The mixture was extracted with dichloromethane (3 x 10 mL) and the organic layers were combined, washed with brine (2 x 10 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/4) to provide 1.00 g (71% yield) of tert-butyl 4-(5-formyl-2- (trifluoromethyl)phenyl)-3 , 6-dihydropyridine- 1 (2H)-carboxylate as yell ow oil. LCMS (ESI, m/z): 356 [M+H].
  • 29
  • [ 372120-55-3 ]
  • 1,1,1,3,3,3-hexafluoropropan-2-yl 1-(3-carbamoyl-4-(trifluoromethyl)benzyl)-1,8-diazaspiro[4.5]decane-8-carboxylate [ No CAS ]
  • 30
  • [ 372120-55-3 ]
  • t-butyl 4-((3-bromo-4-(trifluoromethyl)benzyl)(methyl)amino)-4-methylpiperidine-1-carboxylate [ No CAS ]
  • 31
  • [ 372120-55-3 ]
  • t-butyl 4-((3-(4-fluoropiperidin-1-yl)-4-(trifluoromethyl)benzyl)(methyl)amino)-4-methylpiperidine-1-carboxylate [ No CAS ]
  • 32
  • [ 372120-55-3 ]
  • N-(3-(4-fluoropiperidin-1-yl)-4-(trifluoromethyl)benzyl)-N,4-dimethylpiperidin-4-amine [ No CAS ]
  • 33
  • [ 372120-55-3 ]
  • 4-((3-(4-fluoropiperidin-1-yl)-4-(trifluoromethyl)benzyl)(methyl)amino)-4-methylpiperidine-1-carbonyl chloride [ No CAS ]
  • 34
  • [ 372120-55-3 ]
  • N-(1-(4-((3-(4-fluoropiperidin-1-yl)-4-(trifluoromethyl)benzyl)(methyl)amino)-4-methylpiperidine-1-carbonyl)-1H-pyrazol-3-yl)methanesulfonamide [ No CAS ]
  • 35
  • [ 372120-55-3 ]
  • [ 343788-69-2 ]
  • t-butyl 4-((3-bromo-4-(trifluoromethyl)benzyl)amino)-4-methylpiperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% j00219J A vial was charged with DCE (10 mL), <strong>[372120-55-3]3-bromo-4-(trifluoromethyl)benzaldehyde</strong> (252 mg, 1.00 mmol, 1.00 equiv), t-butyl 4-amino-4-methylpiperidine-1-carboxylate (214 mg, 1.00 mmol,1.00 equiv), and triethylamine (303 mg, 2.99 mmol, 3.00 equiv). The resulting solution was stirred for 1 h at room temperature, then sodium triacetoxyborohydride (636 mg, 3.00 mmol, 3.00 equiv) was added. The mixture was stirred overnight at room temperature and quenched with water (10 mL), as described in Example 1, Step 6. The residue was chromatographed on a silica gel column to provide 300 mg (67% yield) of t-butyl 4-((3-bromo-4-(trifluoromethyl)benzyl)amino)-4- methylpiperidine-1-carboxylate as a yellow oil. LCMS (ESI, m/z): 451 [M+H].
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 372120-55-3 ]

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Chemical Structure| 34328-47-7

A119217 [34328-47-7]

4-Bromo-3-(trifluoromethyl)benzaldehyde

Similarity: 0.98

Chemical Structure| 85118-24-7

A296687 [85118-24-7]

2-Bromo-4-(trifluoromethyl)benzaldehyde

Similarity: 0.96

Chemical Structure| 102684-91-3

A276886 [102684-91-3]

2-Bromo-5-(trifluoromethyl)benzaldehyde

Similarity: 0.94

Chemical Structure| 477535-41-4

A113621 [477535-41-4]

3-Bromo-5-(trifluoromethyl)benzaldehyde

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Chemical Structure| 861928-27-0

A307642 [861928-27-0]

4-Bromo-2-(trifluoromethyl)benzaldehyde

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Aryls

Chemical Structure| 34328-47-7

A119217 [34328-47-7]

4-Bromo-3-(trifluoromethyl)benzaldehyde

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Chemical Structure| 85118-24-7

A296687 [85118-24-7]

2-Bromo-4-(trifluoromethyl)benzaldehyde

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Chemical Structure| 102684-91-3

A276886 [102684-91-3]

2-Bromo-5-(trifluoromethyl)benzaldehyde

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Chemical Structure| 477535-41-4

A113621 [477535-41-4]

3-Bromo-5-(trifluoromethyl)benzaldehyde

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Chemical Structure| 861928-27-0

A307642 [861928-27-0]

4-Bromo-2-(trifluoromethyl)benzaldehyde

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Bromides

Chemical Structure| 34328-47-7

A119217 [34328-47-7]

4-Bromo-3-(trifluoromethyl)benzaldehyde

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Chemical Structure| 85118-24-7

A296687 [85118-24-7]

2-Bromo-4-(trifluoromethyl)benzaldehyde

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Chemical Structure| 102684-91-3

A276886 [102684-91-3]

2-Bromo-5-(trifluoromethyl)benzaldehyde

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Chemical Structure| 477535-41-4

A113621 [477535-41-4]

3-Bromo-5-(trifluoromethyl)benzaldehyde

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Chemical Structure| 861928-27-0

A307642 [861928-27-0]

4-Bromo-2-(trifluoromethyl)benzaldehyde

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Aldehydes

Chemical Structure| 34328-47-7

A119217 [34328-47-7]

4-Bromo-3-(trifluoromethyl)benzaldehyde

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Chemical Structure| 85118-24-7

A296687 [85118-24-7]

2-Bromo-4-(trifluoromethyl)benzaldehyde

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Chemical Structure| 102684-91-3

A276886 [102684-91-3]

2-Bromo-5-(trifluoromethyl)benzaldehyde

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Chemical Structure| 477535-41-4

A113621 [477535-41-4]

3-Bromo-5-(trifluoromethyl)benzaldehyde

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Chemical Structure| 861928-27-0

A307642 [861928-27-0]

4-Bromo-2-(trifluoromethyl)benzaldehyde

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Trifluoromethyls

Chemical Structure| 34328-47-7

A119217 [34328-47-7]

4-Bromo-3-(trifluoromethyl)benzaldehyde

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Chemical Structure| 85118-24-7

A296687 [85118-24-7]

2-Bromo-4-(trifluoromethyl)benzaldehyde

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Chemical Structure| 102684-91-3

A276886 [102684-91-3]

2-Bromo-5-(trifluoromethyl)benzaldehyde

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Chemical Structure| 477535-41-4

A113621 [477535-41-4]

3-Bromo-5-(trifluoromethyl)benzaldehyde

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Chemical Structure| 861928-27-0

A307642 [861928-27-0]

4-Bromo-2-(trifluoromethyl)benzaldehyde

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