[ CAS No. 129822-48-6 ]

Name: 129822-48-6|tert-Butyl 5-chloro-1H-indole-1-carboxylate|98%
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COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 129822-48-6 ]

CAS No. :	129822-48-6	MDL No. :	MFCD05865201
Formula :	C₁₃H₁₄ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GBBULIKZPZSTLA-UHFFFAOYSA-N
M.W :	251.71 g/mol	Pubchem ID :	11459397
Synonyms :

Calculated chemistry of [ 129822-48-6 ]

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 :	69.15
TPSA :	31.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.07 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.2
Log Po/w (XLOGP3) :	3.9
Log Po/w (WLOGP) :	4.08
Log Po/w (MLOGP) :	3.16
Log Po/w (SILICOS-IT) :	2.7
Consensus Log Po/w :	3.41

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.05
Solubility :	0.0224 mg/ml ; 0.0000888 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.25
Solubility :	0.014 mg/ml ; 0.0000557 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.98
Solubility :	0.0265 mg/ml ; 0.000105 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.99

Safety of [ 129822-48-6 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P280-P301+P310	UN#:	2811
Hazard Statements:	H301-H317	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 129822-48-6 ]

* 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 [ 129822-48-6 ]
Downstream synthetic route of [ 129822-48-6 ]

[ 129822-48-6 ] Synthesis Path-Upstream 1~1

1
[ 129822-48-6 ]
[ 73183-34-3 ]
[ 1218790-30-7 ]

Reference： [1] Organometallics, 2014, vol. 33, # 13, p. 3514 - 3522

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[ 129822-48-6 ]

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Yield	Reaction Conditions	Operation in experiment
96%	With dmap In dichloromethane at 25℃;	21.1 Step 1 - Synthesis of tert-butyl 5-chloro-lH-indole-l-carboxylate Step 1 - Synthesis of tert-butyl 5-chloro-lH-indole-l-carboxylate To a solution of 5-chloro-lH-indole (1.5 g, 9.9 mmol) and DMAP (120 mg, 0.99 mmol) in dry DCM (20 mL) Boc20 (3.24 g) was added dropwise, and then the mixture was stirred at 25 °C. The mixture was stirred to at 25 °C for overnight. The solvent was removed by vacuum. The residue was purified by column chromatography (PE : EA = 50 : 1) to give the product of tert-butyl 5-chloro-lH-indole-l-carboxylate (2.4 g, yield: 96%). 1H- MR (CDC13, 400 MHz) δ 7.98 (d, J= 8.0 Hz, 1H), 7.51 (d, J= 4.0 Hz, 1H), 7.44 (d, J= 4.0 Hz, 1H),7.16-7.19 (m, 1H), 6.41 (d, J= 4.0 Hz, 1H), 1.58 (s, 12H). MS (M+H)+: 252.
90%	With dmap In dichloromethane at 20℃; for 14h; Schlenk technique; Inert atmosphere;
84%	With dmap In dichloromethane at 25℃; for 18h; Inert atmosphere;

	With dmap In dichloromethane at 20℃; for 0.75h;
	With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;	A 2-Chloroindole (1.0 g, 6.6 mmol), and di-t-butyldicarbonate (2.2 g, 10 mmol), and Cs2CO3 (3.2 g, 9.9 mmol) were stirred in DMF (30 ml) at room temperature for 4 hr. The reaction mixture was diluted with ethyl acetate and washed with IN HCl (2x), 5% K2CO3 (2x), and brine. The crude product was flash chromatographed (SiO2 gel, 0% to 10% DCM in hexanes gradient) to give tert-buty 5-chloro-lH-indole- 1-carboxylate as a colorless oil. NMR (500 MHz, CDCl3) δ: 1.67 (s, 9H); 6.51 (d, J = 3.7 Hz, IH); 7.26 (dd, J = 2.3, 9 Hz, IH); 7.53 (d, J = 2.3 Hz, IH); 7.61 (d, J = 3.7 Hz, IH); 8.07 (d, J = 9 Hz, IH)
	With triethylamine In tetrahydrofuran for 24h; Reflux;
	With triethylamine In tetrahydrofuran Reflux;	General procedure for the synthesis of 5-substituted-tert-butyl 1H-indole-1-carboxylates (6a-e). General procedure: Di-tert-butyl dicarbonate (8.73 g, 40 mmol) and triethylamine (3.3 mL, 23.7 mmol) were added to a solution of appropriate indoles 4a-e (20 mmol) in tetrahydrofuran (10 mL). The reaction mixture was heated under reflux for 24-48 h. After cooling the solvent was evaporated under reduced pressure and the residue (derivatives 6a and 6c) was purified by column chromatography using dichloromethane or dichloromethane/petroleum ether (9/1) as eluent or recrystallized with ethanol (derivatives 6b, 6d, 6e). For compounds 6a,c-e see supporting information. Derivatives 6b, 6c and 6e were also reported with a different method [33].

Yield	Reaction Conditions	Operation in experiment
98%	In 2,2,2-trifluoroethanol at 150℃; for 1h; microwave irradiation;
98%	With 2,2,2-trifluoroethanol at 150℃; for 1h; Microwave irradiation;	2 EXAMPLE 2; Following the procedure set forth in Example 1 (A) above, indole derivatives were deprotected using TFE or HFIP in a microwave reactor at 150° C. as set forth in Table 1 below.
98%	With 2,2,2-trifluoroethanol at 150℃; for 1h; Microwave irradiation;	1.A; 2 Example 1; (A) A solution of the N-Boc protected amine (1 mmol) in TFE (2,2,2-trifluoroethanol) or HFIP (hexafluoroisopropanol) (5 mL) was placed in a sealed microwave vial. The reaction mixture was heated (100°C or 150°C) in a Biotage - Initiator Sixty microwave reactor with stirring until the disappearance of the starting material was observed. After cooling to room temperature, the mixture was evaporated to dryness under reduced pressure. The crude product was purified by flash-column chromatography. 1H NMR and 13C NMR were measured on Bruker Avance DPX-300 NMR or Bruker Avance-300 NMR spectrometers, operating at a proton (1H) frequency of 300.13 MHz and carbon (13C) frequency of 75.43 MHz.Example 2 Following the procedure set forth in Example 1(A) above, indole derivatives were deprotected using TFE or HFIP in a microwave reactor at 150°C as set forth in Table 1 below.

Yield	Reaction Conditions	Operation in experiment
73%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium acetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; Inert atmosphere;	21.2 Step 2 - Synthesis of tert-butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole-l- carboxylate Step 2 - Synthesis of tert-butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole-l- carboxylateTo a degassed solution of tert-butyl 5-chloro-lH-indole-l -carboxylate (1.0 g, 3.97 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (1.11 g, 4.37 mmol) in dry DMF (10 mL) was added Pd(dba)3 (10 mg), x-Phos (10 mg) and AcOK (780 mg, 7.95 mmol) under N2. The mixture was heated to 100 °C and then stirred overnight. The reaction mixture was cooled to RT and filtered. The filtrate was washed with EA, brine, dried over Na2S04.After concentrated, the residue was purified by column (PE : EA = 50 : 1) to give the product of tert-butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole-l-carboxylate (1.0 g, yield: 73%). 1H- MR (CDC13, 400 MHz) δ 8.12 (d, J= 8.0 Hz, 1H), 8.04 (s, 1H), 7.74 (d, J= 12.0 Hz, 1H), 7.54 (d, J= 4.0 Hz, 1H), 6.54 (d, J= 4.0 Hz, 1H), 1.65 (s, 9H), 1.35 (s, 12H). MS (M+H)+: 344.
24%	With cerium(III) chloride; tetraethylammonium chloride In acetonitrile at 20℃; for 24h; Irradiation; Inert atmosphere; Sealed tube;
23.3 mg	With pyridine; 9,10-Dicyanoanthracene; tert-butylammonium hexafluorophosphate(V) In acetonitrile at 22℃; for 12h; Inert atmosphere; Electrolysis; Irradiation;

[ CAS No. 129822-48-6 ]

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