676448-17-2|1-Boc-4-Bromoindole| Ambeed

Structure of 676448-17-2

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Quality Control of [ 676448-17-2 ] Purity: 97% SDS Specification

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Product Details of [ 676448-17-2 ]

CAS No. :	676448-17-2
Formula :	C₁₃H₁₄BrNO₂
M.W :	296.16
SMILES Code :	C(C)(C)(C)OC(=O)[N]2C1=CC=CC(=C1C=C2)Br
MDL No. :	MFCD04117874
InChI Key :	ZGBNKNOAADXGOH-UHFFFAOYSA-N
Pubchem ID :	40425427

Safety of [ 676448-17-2 ]

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

Computational Chemistry of [ 676448-17-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	9
Fraction Csp3	0.31
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	71.84
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	31.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.26
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.96
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.19
Log P_o/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.	3.29
Log P_o/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	2.74
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.49

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.36
Solubility	0.0128 mg/ml ; 0.0000432 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.32
Solubility	0.0143 mg/ml ; 0.0000483 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-4.2
Solubility	0.0187 mg/ml ; 0.0000631 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	Yes
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	Yes
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.	-5.29 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)	2.19

Application In Synthesis of [ 676448-17-2 ]

* 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 [ 676448-17-2 ]

[ 676448-17-2 ] Synthesis Path-Downstream 1~35

1
[ 52488-36-5 ]
[ 34619-03-9 ]
[ 676448-17-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydride; In tetrahydrofuran; mineral oil; for 22h;	Add DI-TERT-BUTYL dicarbonate (1.4 g. 6.4 mmol) and sodium hydride (0.15 g, 60% dispersion in mineral oil, 3.8 mmol) to a solution of 4-bromoindole (0.4 mL, 3.2 mmol) in THF (11 mL) at 0 C. Stir the reaction for 22 h, quench with saturated aqueous ammonium chloride, and extract with methylene chloride. Dry the combined organic extracts with sodium sulfate, filter, and concentrate in vacuo. Purify by flash column chromatography, utilizing the appropriate mixture of hexanes and methylene chloride, to provide 0.85 g (90%) of the titled compound as a clear, colorless OIL.'H NMR (CDC13) 8 8. 10 (d, J = 8 HZ, 1H), 7.63 (d, J = 4 Hz, 1H), 7. 38 (d, J = 8 HZ, 1H), 7.16 (t, J = 8 Hz, 1H), 6.64 (d, J = 4 Hz, 1H), 1.67 (s, 9H). TLC (SI02) : Rf 0. 3 (9: 1 hexanes/methylene chloride).

References: [1]Patent: WO2004/50659,2004,A1 .Location in patent: Page 95-96.

2
[ 52488-36-5 ]
[ 24424-99-5 ]
[ 676448-17-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With dmap; In tetrahydrofuran; for 0.25h;	Di-tert-butyl dicarbonate (17 g, 76.5 mmol) was added to a solution of 4-Bromoindole 4-1 (10 g, 51 mmol) and DMAP (0.62 g, 0.51 mmol) in THF (120 mL). The reaction mixture was stirred for 15 minutes, and then stripped. The remaining oil was partitioned between ether and water. The ether layer was washed with 350 mL of saturated sodium bicarbonate and 175 mL of brine. The ether layer was dried over magnesium sulfate, filtered and stripped. The remaining brown oil was chromatographed over silica gel eluding with 1:100 ethyl acetate: hexanes to afford 15 g (100% yield) of 4-bromo-indole-1-carboxylic acid-tert-butyl ester 4-2.
99%	In dichloromethane; at 20℃; for 8h;	To a solution of 4-bromoindole (1.96 g, 10 mmol) in dichloromethane (50 mL),DMAP (122 mg, 1 mmol) and di-tert-butyl dicarbonate (2.4 g, 11 mmol) were added,The reaction system is stirred at room temperature for 8 hours.Work-up gave tert-butyl 4-bromo-1H-indol-1-yl carbonate (2.96 g, 99% yield).
95%	With dmap; In dichloromethane; at 20℃; for 0.25h;Inert atmosphere; Sealed tube;	Boc2O (3.5 mL, 15.3 mmol) was added to a stirred solution of 4-bromo-1H-indole (2 g, 10.2 mmol) and 4-DMAP (62 mg, 0.5 mmol) in dichloromethane (30 mL). The reaction mixture was stirred at ambient temperature for 15 min. Water (40 mL) was added and the layers were separated. Aqueous phase was extracted with additional dichloromethane (30 mL). The combined organic extracts were washed with water, aqueous sodium chloride solution, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography (0-2% ethyl acetate in pet-ether) to afford compound 4 (2.86 g, 95% yield) as a colour less liquid. 1H NMR (CDCl3, 400 MHz): delta 1.67 (S, 9H), 6.63 (d, 1H, J=3.6 Hz), 7.16 (t, 1H, J=8 Hz), 7.38 (d, 1H, J=8 Hz), 7.64 (d, 1H, J=3.6 Hz), 8.11 (d, 1H, J=8.4 Hz). 13C NMR (CDCl3, 100 MHz): delta 28.13, 84.23, 107.06, 114.22, 114.66, 125.11, 125.52, 126.44, 131.12, 135.55, 149.43

85%	With dmap; triethylamine; In acetonitrile; at 20℃; for 2h;	Step 84a: 7¾rt-butyl 4-bromo-lH-indole-l-carboxylate (Compound 0601-176)The solution of 4-bromoindole (394 mg, 2.00 mmol), (Boc)20 (523 mg, 2.40 mmol), DMAP (293 mg, 2.4 mmol) and Et3N (0.4 mL) in MeCN (6 mL) was stirred at room temperature for 2 hours. The solvent was removed and the residue was dissolved in ethyl acetate (40 mL), washed with water (3 x 20 mL) and brine (1 x 20 mL), the organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to afford compound 0601-176 (508 mg, 85%) as a colorless oil. 1H-NMR (400 MHz.OMSO-d6) delta 1.64 (s, 9H), 6.67 (d, J= 3.2 Hz, 1H), 7.28 (t, J= 8.0 Hz, 1H), 7.48 (m, 1H),7.80 (d, J= 3.2 Hz, 1H), 8.08 (m, 1H).
85%	With dmap; triethylamine; In acetonitrile; at 20℃; for 2h;	Step 84a: Tert-butyl 4-bromo-1H-indole-1-carboxylate (Compound 0601-176)[0559]The solution of 4-bromoindole (394 mg, 2.00 mmol), (Boc)2O (523 mg, 2.40 mmol), DMAP (293 mg, 2.4 mmol) and Et3N (0.4 mL) in MeCN (6 mL) was stirred at room temperature for 2 hours. The solvent was removed and the residue was dissolved in ethyl acetate (40 mL), washed with water (3×20 mL) and brine (1×20 mL), the organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to afford compound 0601-176 (508 mg, 85%) as a colorless oil. 1H-NMR (400 MHz. DMSO-d6) delta 1.64 (s, 9H), 6.67 (d, J=3.2 Hz, 1H), 7.28 (t, J=8.0 Hz, 1H), 7.48 (m, 1H), 7.80 (d, J=3.2 Hz, 1H), 8.08 (m, 1H).
85%	With dmap; triethylamine; In acetonitrile; at 20℃; for 2h;	MeCN (6 mL) solution of 4-bromo-indole (394mg, 2.00mmol), (Boc) 2O (523mg, 2.40mmol), was DMAP (293mg, 2.4mmol) to a solution of and Et3N (0.4mL) was stirred at room temperature for 2 hours . The solvent was removed and the residue was dissolved in ethyl acetate (40 mL), washed with water (3 × 20 mL) and brine (1X20mL), and the organic layer concentrated, and purified by column chromatography on silica gel (petroleum ether) on, to give compound 0601-176 as a colorless oil (508mg, 85%).
76%	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	To a solution of 4-bromo-lH-indole (LXXXVII) (10 g, 50.8 mmol, 1 eq), DMAP (622 mg, 5.1 mmol, 0.1 eq) and TEA (10.6 ml, 76.1 mmol, 3 eq) in DCM (200 mL) was added B0C2O (14.4 mL, 61 mmol, 1.2 eq) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (200 mL) was added and the mixture was extracted with DCM twice. The solvent was evaporated under vacuum to give fert-butyl 4-bromo-lH-indole-l-carboxylate (LXXXVIII) as white solid (11.4 g, 38.5 mmol, 76% yield). NMR (CDC13, 400 MHz) delta ppm 1.68 (s, 9H), 6.64 (d, J=4Hz, 1H), 7.17 (t, J=8.4Hz, 1H), 7.39 (d, J=7.6Hz, 1H), 7.64 (d, J=3.2Hz, 1H), 8.11 (d, J=8.0Hz, 1H); ESIMS found for Ci3Hi4BrN02 mlz 297.1 (M+H).
76%	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	To a solution of 4-bromo-1H-indole (LXX) (10 g, 50.8 mmol, 1 eq), DMAP (622 mg, 5.1 mmol, 0.1 eq) and TEA (10.6 ml, 76.1 mmol, 3 eq) in DCM (200 mL) was added Boc2O (14.4 mL, 61 mmol, 1.2 eq) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (200 mL) was added and the mixture was extracted with DCM twice. The solvent was evaporated under vacuum to give tert-butyl 4-bromo-1H-indole-1-carboxylate (LXXI) as white solid (11.4 g, 38.5 mmol, 76% yield). 1H NMR (CDCI3, 400 MHz) delta ppm 1.68 (s, 9H), 6.64 (d, J=4Hz, 1H), 7.17 (t, J=8.4Hz, 1H), 7.39 (d, J=7.6Hz, 1H), 7.64 (d, J=3.2Hz, 1H), 8.11 (d, J=8.0Hz, 1H); ESIMS found for C13H14BrNO2 m/z 297.1 (M+H).
76%	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	To a solution of 4-bromo-1H-indole (LXX) (10 g, 50.8 mmol, 1 eq), DMAP (622 mg, 5.1 mmol, 0.1 eq) and TEA (10.6 ml, 76.1 mmol, 3 eq) in DCM (200 mL) was added Boc2O (14.4 mL, 61 mmol, 1.2 eq) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (200 mL) was added and the mixture was extracted with DCM twice. The solvent was evaporated under vacuum to give tert-butyl 4-bromo- 1H-indole- 1 -carboxylate (LXXI) as white solid (11.4 g, 38.5 mmol, 76% yield). ?HNMR(CDC13, 400 MHz) Eppm 1.68 (s, 9H), 6.64 (d,J=4Hz, 1H), 7.17 (t,J=8.4Hz, 1H), 7.39 (d,J=7.6Hz, 1H), 7.64 (d,J=3.2Hz, 1H), 8.11 (d, J8.OHz, 1H); ESIMS found for C,3H,4BrNO2 mlz 297.1 (M+H).
66.19%		To a suspension of 60% NaH (0.449 g, 11.2 mmol) in dry THF (20.0 mL) was added a solution of compound 1 (2.000 g, 10.20 mmol) in THF (20.0 mL) at -78 C. The reaction mixture was stirred for 1 h. A solution of ditertiary butyl dicarbonate (2.58 mL, 11.2 mmol) in THF (20.0 mL) was added to the above solution drop-wise at -78 C. and stirred at rt for 16 h The reaction progress was monitored by diluting an aliquot of the reaction mixture with water and extracting with EtOAc. The organic layer was spotted over an analytical silica gel TLC plate and visualized using 254 nm UV light. The reaction progressed to completion with the formation of a non-polar spot. The Rf values of the starting material and product were 0.3 and 0.5, respectively. The reaction mixture was poured into ice water (75.0 mL) and extracted with EtOAc (2×100.0 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude compound 2. The crude compound was purified by flash column using 230-400 mesh silica gel and eluted with 8% EtOAc in petroleum ether to afford compound 2 as a brown liquid. TLC system: 5% EtOAc in petroleum ether. Yield 2.000 g (66.19%).
	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	To a solution of 4-bromo-lH-indole (LXX) (10 g, 50.8 mmol, 1 eq), DMAP (622 mg, 5.1 mmol, 0.1 eq) and TEA (10.6 ml, 76.1 mmol, 3 eq) in DCM (200 mL) was added B0C2O (14.4 mL, 61 mmol, 1.2 eq) at 0C. The reaction was warmed to room temperature and stirred for 2 hours. Water (200 mL) was added and the mixture was extracted with DCM twice. The solvent was evaporated under vacuum to give fert-butyl 4-bromo-lH-indole-l-carboxylate (LXXI) as white solid (11.4 g, 38.5 mmol, 76% yield). NMR (CDC13, 400 MHz) delta ppm 1.68 (s, 9H), 6.64 (d, J=4Hz, 1H), 7.17 (t, J=8.4Hz, 1H), 7.39 (d, J=7.6Hz, 1H), 7.64 (d, J=3.2Hz, 1H), 8.11 (d, J=8.0Hz, 1H); ESIMS found for Ci3Hi4BrN02 mlz 297.1 (M+H).
	With dmap; In tetrahydrofuran; for 0.5h;	Di-tert-butyl dicarbonate (5.33 mL, 22.95 mmol) was added to a solution of 4-bromo-1H-indole (3.00 g, 15.30 mmol) and DMAP (4-dimethylaminopyridine) (0.187 g, 1.530 mmol)) in tetrahydrofuran (20 mL). The reaction mixture was stirred for 30 minutes. The mixture was partitioned between ether (100 mL) and water (100 mL). The ether layer was washed with (3*50 mL) of saturated aqueous sodium bicarbonate and 75 mL of brine. The ether layer was dried over magnesium sulfate, filtered and concentrated. The residue was chromatographed over silica gel eluting with 1:100 ethyl acetate: petroleum ether to afford the title compound.

References: [1]Patent: US2004/72844,2004,A1 .Location in patent: Page/Page column 13-14.
[2]Patent: CN107973780,2018,A .Location in patent: Paragraph 0233; 0234; 0235; 0236.
[3]Tetrahedron,2009,vol. 65,p. 6877 - 6881.
[4]Journal of Medicinal Chemistry,2015,vol. 58,p. 9179 - 9195.
[5]Tetrahedron Letters,2017,vol. 58,p. 1499 - 1500.
[6]Synthesis,2009,p. 3617 - 3632.
[7]Patent: WO2011/130628,2011,A1 .Location in patent: Page/Page column 223.
[8]Patent: US2013/102595,2013,A1 .Location in patent: Paragraph 0558; 0559.
[9]Patent: JP2015/187145,2015,A .Location in patent: Paragraph 0475.
[10]Patent: WO2017/23986,2017,A1 .Location in patent: Paragraph 0694; 0695.
[11]Patent: WO2017/23973,2017,A1 .Location in patent: Paragraph 0693.
[12]Patent: WO2017/24026,2017,A1 .Location in patent: Paragraph 0675; 0676.
[13]Patent: US2016/9706,2016,A1 .Location in patent: Paragraph 0314; 0315.
[14]Patent: WO2017/23993,2017,A1 .Location in patent: Paragraph 0676; 0677.
[15]Patent: US2019/77784,2019,A1 .Location in patent: Paragraph 2104.

3
[ 52488-36-5 ]
[ 6627-89-0 ]
[ 676448-17-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; for 18h;	A solution of 0.48 mL (3.8 mmol) of 4-bromo-lH-indole in 1 mL of THF was added to a suspension of 0.15 g (6.3 mmol) of NaH in 5 mL of THF, followed by 1.2 mL (6.3 mmol) of tert-butyl phenylcarbonate. The reaction solution was stirred 18 h, then quenched with1 mL of iPrOH, poured into 100 mL of Et2O and washed twice with a saturated aqueous solution of NH4Cl and thrice with water. The organic solvent was removed in vacuo and the residue was purified by flash chromatography eluting with neat hexane to yield the title compound. MS (M-BOC+2H)+ 196.

References: [1]Patent: WO2006/66172,2006,A1 .Location in patent: Page/Page column 78-79.

4
[ 676448-17-2 ]
[ 79099-07-3 ]
[ 676448-18-3 ]

Yield	Reaction Conditions	Operation in experiment
19%		A solution of <strong>[676448-17-2]4-bromo-indole-1-carboxylic acid-tert-butyl ester</strong> 4-2 (4.9 g, 16.5 mmol) in THF (150 mL) under Argon was cooled to -70 C., and n-BuLi (12.4 mL, 24.8 mmol) was added over 20 min. The reaction mixture was warmed to -5 C. in an ice bath and was stirred at this temperature for 30 min. The mixture was cooled to -70 C. and a solution of N-Boc-piperidone 4-3 (3.3 g, 16.5 mmol) in THF (10 mL) was added over 15 min. The reaction was stirred for 45 min at -70 C. and was then warmed to room temperature. The reaction was quenched with a saturated solution of ammonium chloride (75 mL) and partitioned between water (25 mL) and ethyl acetate (75 mL). The organic layer was washed with water (50 mL) and brine (50 mL), then dried (MgSO4), filtered and concentrated. The remaining brown oil was chromatographed, eluding with ethyl acetate:hexanes (1:9) to afford 1.32 g (19% yield) of 4-(1-tert-butoxycarbonyl-4-hydroxy-piperidin-4-yl)-indole-1-carboxylic acid tert-butyl ester 4-4.

References: [1]Patent: US2004/72844,2004,A1 .Location in patent: Page/Page column 15.

5
[ 676448-17-2 ]
[ 957034-29-6 ]

References: [1]Tetrahedron,2009,vol. 65,p. 6877 - 6881.

6
[ 676448-17-2 ]
[ 1196150-98-7 ]

References: [1]Organic Letters,2009,vol. 11,p. 5330 - 5333.

7
[ 3934-20-1 ]
[ 676448-17-2 ]
[ 1205744-88-2 ]

References: [1]Synthesis,2009,p. 3617 - 3632.

8
[ 676448-17-2 ]
[ 7486-35-3 ]
t-butyl 4-vinyl-1H-indole-1-carboxylate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5693 - 5697.

9
[ 1195931-67-9 ]
[ 676448-17-2 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 14076 - 14078.

10
[ 676448-17-2 ]
[ 67-64-1 ]
[ 1284216-73-4 ]

References: [1]Journal of the American Chemical Society,2011,vol. 133,p. 5194 - 5197.

11
[ 676448-17-2 ]
[ 1350615-54-1 ]
[ 1350615-68-7 ]

Yield	Reaction Conditions	Operation in experiment
41%	With bis-triphenylphosphine-palladium(II) chloride; lithium chloride; In 1,2-dimethoxyethane; at 130℃; for 0.583333h;Inert atmosphere; Microwave irradiation;	Bis(triphenylphosphine)palladium (II) chloride (2.487 mg, 3.54 .mol) was added to astirred mixture of 3-(tributylstannyl)-7-(triisopropylsilyl)-[1,2,3]triazolo[1,5-a]pyridine(10, 100 mg, 0.18 mmol) and <strong>[676448-17-2]tert-butyl 4-bromo-1H-indole-1-carboxylate</strong> (52.5 mg, 0.18mmol) and lithium chloride (22.53 mg, 0.53 mmol) dissolved in DME (1 mL) anddegased and purged with argon. The resulting mixture was heated at 130 C for 35minutes in the microwave. The mixture was evaporated under reduce pressure. Thereaction mixture was purified by preparative HPLC using a Waters X-Bridge reversephasecolumn (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40ml / minute) and decreasingly polar mixtures of water (containing 0.2% ammoniumcarbonate) and acetonitrile as eluent. The fractions containing the desired compound wereevaporated to dryness to afford tert-butyl 4-(7-(triisopropylsilyl)-[1,2,3]triazolo[1,5-a]pyridin-3-yl)-1H-indole-1-carboxylate (35.6 mg, 41%) as a white solid.

References: [1]Tetrahedron Letters,2011,vol. 52,p. 6376 - 6378.

12
[ 676448-17-2 ]
[ 13411-48-8 ]
[ 88059-20-5 ]

References: [1]Organic Letters,2014,vol. 16,p. 824 - 827.

13
[ 35812-01-2 ]
[ 676448-17-2 ]
C₂₀H₁₇BrN₂O₅S [ No CAS ]

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 14231 - 14234.

14
[ 676448-17-2 ]
C₁₂H₁₈O₃ [ No CAS ]
C₂₅H₃₁NO₅ [ No CAS ]

References: [1]Organic Letters,2015,vol. 17,p. 5432 - 5435.

15
[ 676448-17-2 ]
C₁₂H₁₈O₃ [ No CAS ]
C₂₀H₂₃NO₃ [ No CAS ]

References: [1]Organic Letters,2015,vol. 17,p. 5432 - 5435.

16
[ 676448-17-2 ]
tert-butyl 4-(4-(2-hydroxyethyl)piperazin-1-yl)-1H-indole-1-carboxylate [ No CAS ]