[ CAS No. 1805-65-8 ] {[proInfo.proName]}

Name: 1805-65-8|2-(tert-Butyl)-1H-indole|97%
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SKU: A967196
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 1805-65-8 ]

CAS No. :	1805-65-8	MDL No. :	MFCD04004060
Formula :	C₁₂H₁₅N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WVPGIDWFLXGCLA-UHFFFAOYSA-N
M.W :	173.25	Pubchem ID :	594166
Synonyms :

Calculated chemistry of [ 1805-65-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.33
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.57
TPSA :	15.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.42
Log Po/w (XLOGP3) :	3.76
Log Po/w (WLOGP) :	3.47
Log Po/w (MLOGP) :	2.76
Log Po/w (SILICOS-IT) :	3.69
Consensus Log Po/w :	3.22

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.73
Solubility :	0.0323 mg/ml ; 0.000187 mol/l
Class :	Soluble
Log S (Ali) :	-3.78
Solubility :	0.0285 mg/ml ; 0.000164 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.49
Solubility :	0.00562 mg/ml ; 0.0000324 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.44

Safety of [ 1805-65-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1805-65-8 ]

* 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.

Upstream synthesis route of [ 1805-65-8 ]
Downstream synthetic route of [ 1805-65-8 ]

[ 1805-65-8 ] Synthesis Path-Upstream 1~1

1
[ 1805-65-8 ]
[ 174274-85-2 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 4, p. 892 - 903

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Yield	Reaction Conditions	Operation in experiment
95%	With n-butyllithium; In tetrahydrofuran; hexane; at 20℃;Inert atmosphere;	Example 8. Synthesis of 2-tert-butyl-1 H-lndole. In a one L flask, a solution of N-o-Tolylpivalamide (35g, 0.183 mol, 1 eq) (obtained in Example 7) in dry THF (120 mL) was made under inert atmosphere. After cooling in a water bath, n- butyllithium (2.5 M in hexane, 220 mL, 0.55 mol, 3 eq) was added dropwise. The reaction mixture was stirred overnight at room temperature, after which it was cooled in an ice bath. Once the solution was cooled, saturated aqueous ammonium chloride solution (340 mL) was added slowly. The water phase was extracted with ethyl acetate (340 mL), after which the combined organic phases were dried on magnesium sulfate and concentrated in vacuo, to afford a brown solid (95%). MW.: 173.25 g/mol. 1H-NMR (500 MHz, CDCI3): delta (ppm) = 1 .32 (s, 9H, C(CH3)3), 6.18 (d, 1 H, t-Bu C-CH), 7.02 (m, 2H, ArH), 7.24 (d, 1 H, ArH), 7.46 (d, 1 H, ArH), 7.87 (br. s, 1 H, NH). 13C-NMR (125 MHz, CDCI3): delta (ppm) = 30.33 (CH3), 31 .84 (C), 96.96 (CH), 1 10.34 (CH), 1 19.60 (CH), 1 19.98 (CH), 121 .07 (CH), 128.51 (C), 135.76 (C), 148.77 (C).
88%	With n-butyllithium; In tetrahydrofuran; hexane; at 15℃;	To a solution of N-o-tolylpivalamide (30.0 g, 159 mmol) in dry THF (100 mL) was added dropwise n-BuLi (2.5 M in hexane, 190 mL) at 15 C. After addition, the mixture was stirred overnight at 15 C. The mixture was cooled in an ice-water bath and treated with saturated NH4Cl. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography on silica gel to give 2-tert-butyl-1H-indole (24 g, 88%). 1H NMR (300 MHz, CDCl3) delta 7.99 (br. s, 1H), 7.54 (d, J=7.2 Hz, 1H), 7.05 (d, J=7.8 Hz, 1H), 7.06-7.13 (m, 2H), 6.26 (s, 1H), 1.39 (s, 9H).
88%	With n-butyllithium; ammonium chloride; In tetrahydrofuran; hexane;	2-tert-Butyl-1H-indole To a solution of 2,2-dimethyl-N-o-tolyl-propionamide (30.0 g, 159 mmol) in dry THF (100 mL) was added dropwise n-BuLi (2.5 M, in hexane, 190 mL) at 15 C. The mixture was stirred overnight at 15 C., cooled in an ice-water bath and treated with saturated NH4Cl solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography to give 2-tert-butyl-1H-indole (23.8 g, 88%).

88%	With n-butyllithium; ammonium chloride; In tetrahydrofuran; hexane;	2-tert-Butyl-1H-indole To a solution of N-o-tolylpivalamide (30.0 g, 159 mmol) in dry THF (100 mL) was added dropwise n-BuLi (2.5 M in hexane, 190 mL) at 15 C. After addition, the mixture was stirred overnight at 15 C. The mixture was cooled in an ice-water bath and treated with saturated NH4Cl. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography on silica gel to give 2-tert-butyl-1H-indole (24 g, 88%). 1H NMR (300 MHz, CDCl3) delta 7.99 (br. s, 1H), 7.54 (d, J=7.2 Hz, 1H), 7.05 (d, J=7.8 Hz, 1H), 7.06-7.13 (m, 2H), 6.26 (s, 1H), 1.39 (s, 9H).
88%	With n-butyllithium; In tetrahydrofuran; hexane; at 15℃;	To a solution of 2,2-dimethyl-N-o-tolyl-propionamide (30.0 g, 159 mmol) in dry THF (100 mL) was added dropwise n-BuLi (2.5 M, in hexane, 190 mL) at 15 C. The mixture was stirred overnight at 15 C., cooled in an ice-water bath and treated with saturated NH4Cl solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography to give 2-tert-butyl-1H-indole (23.8 g, 88%).
88%	With n-butyllithium; In tetrahydrofuran; hexane; at 15℃;	To a solution of 2,2-dimethyl-N-o-tolyl-propionamide (30.0 g, 159 mmol) in dry THF (100 mL) was added dropwise n-BuLi (2.5 M, in hexane, 190 mL) at 15 C. The mixture was stirred overnight at 15 C., cooled in an ice-water bath and treated with saturated NH4Cl solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography to give 2-tert-butyl-1H-indole (23.8 g, 88%).
	With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 23℃;Inert atmosphere;	General procedure: The above product was added to a dried RBF under argon (5.3 mmol) in THF (7 mL) and nBuLi (654mg, 16 mmol, 2.5M solution in hexanes) was added drop wise. The solution was allowed to stir at RT overnight. The solution was quenched with NH4Cl (5 mL) and the aqueous layer was collected. The aqueous layer was then extracted with EtOAc (3x 25mL) and the combined organic extracts were dried over anhydrous MgSO4 and concentrated under vacuum. The residue was then purified by flash chromatography using 20% EtOAc in Hexanes giving desired indole (85-95%).

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; acetic acid; at 10℃; for 0.333333h;	To a solution of <strong>[1805-65-8]2-tert-butyl-1H-indole</strong> (10 g, 48 mmol) in AcOH (40 mL) was added NaBH4 at 10 C. The mixture was stirred for 20 minutes at 10 C. before being treated dropwise with H2O under ice cooling. The mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give 2-tert-butylindoline (9.8 g), which was used directly in the next step.
	With sodium tetrahydroborate; In water; acetic acid;	2-tert-Butyl-2,3-dihydro-1H-indole To a solution of <strong>[1805-65-8]2-tert-butyl-1H-indole</strong> (5.0 g, 29 mmol) in AcOH (20 mL) was added NaBH4 at 10 C. The mixture was stirred for 20 min at 10 C., treated dropwise with H2O under ice cooling, and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give a mixture of starting material and 2-tert-butyl-2,3-dihydro-1H-indole (4.9 g), which was used directly in the next step.
	With sodium tetrahydroborate; In water; acetic acid;	2-tert-Butylindoline To a solution of <strong>[1805-65-8]2-tert-butyl-1H-indole</strong> (10 g, 48 mmol) in AcOH (40 mL) was added NaBH4 at 10 C. The mixture was stirred for 20 minutes at 10 C. before being treated dropwise with H2O under ice cooling. The mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give 2-tert-butylindoline (9.8 g), which was used directly in the next step.

	With sodium tetrahydroborate; acetic acid; at 10℃; for 0.333333h;	To a solution of <strong>[1805-65-8]2-tert-butyl-1H-indole</strong> (5.0 g, 29 mmol) in AcOH (20 mL) was added NaBH4 at 10 C. The mixture was stirred for 20 min at 10 C., treated dropwise with H2O under ice cooling, and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give a mixture of starting material and 2-tert-butyl-2,3-dihydro-1H-indole (4.9 g), which was used directly in the next step.
9.8 g	With sodium tetrahydroborate; acetic acid; In water; at 10℃; for 0.333333h;	To a solution of <strong>[1805-65-8]2-tert-butyl-1H-indole</strong> (10 g, 48 mmol) in AcOH (40 mL) was added NaBH4 at 10 C. The mixture was stirred for 20 minutes at 10 C. before being treated dropwise with H2O under ice cooling. The mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give 2-tert-butylindoline (9.8 g), which was used directly in the next step.

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