352359-22-9|(1-(tert-Butoxycarbonyl)-6-chloro-1H-indol-2-yl)boronic acid| Ambeed

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Quality Control of [ 352359-22-9 ] Purity: 98% SDS Specification

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Product Details of [ 352359-22-9 ]

CAS No. :	352359-22-9
Formula :	C₁₃H₁₅BClNO₄
M.W :	295.53
SMILES Code :	CC(C)(C)OC(=O)N1C(=CC2=C1C=C(Cl)C=C2)B(O)O
MDL No. :	MFCD08689539
InChI Key :	AHUWHEZTYPWOCY-UHFFFAOYSA-N
Pubchem ID :	44119151

Safety of [ 352359-22-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 352359-22-9 ]

* 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 [ 352359-22-9 ]

[ 352359-22-9 ] Synthesis Path-Downstream 1~30

1
[ 323580-68-3 ]
[ 352359-22-9 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 6-chloro-indole-l -carboxylic acid tert-butyl ester (2 g) in dry THF (10 mL) is added triisopropyl borate (2.74 mL) under N2. The mixture is cooled to O0C in an ice bath. Lithium diisopropylamine (4.97 mL, 2 M) is added over an hour at 0C. The reaction is stirred at O0C for 30 minutes. 2 N HCl (IO mL) is added. The resulting mixture is extracted with EtOAc. The organic layer is dried, filtered and concentrate. The residue is purified by flash chromatography on silica gel eluting with 5% to 60% EtOAc in heptane to afford 1 -ffert-butoxycarbonyD--chloro- 1 H-indol-2- ylboronic acid as a solid (1 g).

References: [1]Patent: WO2006/81343,2006,A1 .Location in patent: Page/Page column 77.

3
[ 113118-81-3 ]
[ 352359-22-9 ]
[ 1202550-14-8 ]

Yield	Reaction Conditions	Operation in experiment
		A flask is charged with Λ/-(tert-butoxycarbonyl)-6-chloro-1 H-indol-2-ylboronic acid (8.3 g, 28.1 mmol), 5-bromonicotinaldehyde (4.35 g, 23.4 mmol), K3PO4 (9.94 g, 46.8 mmol), s-Phos (0.480 g, 1.170 mmol) and Pd2(dba)3 (0.429 g, 0.468 mmol), and the flask is flushed with N2. Toluene (250 ml.) is added, and the mixture is heated to 85 0C for 1.5 h.The mixture is cooled to room temperature. Ethyl acetate (250 ml.) is added and the mixture is filtered through a pad of silica gel, which is washed with EtOAc. Silica gel is added to the combined filtrate, which is concentrated in vacuo. The residue is placed under high vacuum at 63 0C overnight, and after elution with ethyl acetate, 5-(6-chloro- <n="135"/>1 H-indol-2-yl)-pyridine-3-carbaldehyde is obtained. MS (ESI) m/z 257.0 and 258.9 (M+H)+.

References: [1]Patent: WO2009/156462,2009,A2 .Location in patent: Page/Page column 133-134.

4
[ 352359-22-9 ]
[ 130722-95-1 ]
[ 1202550-06-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; for 3.5h;Inert atmosphere;	A flask is charged with θ-chloro-i-Boc-indole^-boronic acid (0.839 g, 2.83 mmol), 1- benzyloxy-3-bromo-pyridine (0.500 g, 1.89 mmol), potassium phosphate (1.2 g, 5.67 mmol) and DMF (5 ml_). The flask is evacuated and filled with nitrogen thrice and Pd(PPh3)4 (0.164 g, 0.141 mmol) is added. The flask is evacuated and filled with nitrogen thrice again, and heated to 80 C for 3.5 h. The mixture is then diluted with ethyl acetate and washed with water thrice. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is redissolved in DCM (1 ml_) and trifluoroacetic acid (2 ml.) is added. After 1 h, 4M aqueous NaOH is added and following extraction with DCM, the organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica gel flash chromatography (heptane- ethyl acetate, 1 :1) to afford 2-(3-benzyloxy-phenyl)-6-chloro-1 H-indole as a yellow solid. MS (ESI) m/z 335.07 (M+H)+.

References: [1]Patent: WO2009/156462,2009,A2 .Location in patent: Page/Page column 131.

5
[ 74115-13-2 ]
[ 352359-22-9 ]
[ 1202552-02-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 110℃; for 1.5h;Microwave irradiation; Inert atmosphere;	A microwave flask is charged with 6-chloro-1-Boc-indole-2-boronic acid (1.91 g, 6.46 mmol), 3-hydroxy-5-bromopyridine (0.750 g, 4.31 mmol), potassium phosphate (1.83 g, 8.62 mmol) and DMF (15 ml_). The flask is evacuated and filled with nitrogen thrice and <n="164"/>Pd(PPh3)4 (0.250 g, 0.215 mmol) is added. The flask is evacuated and filled with nitrogen thrice again, and heated to 110 C under microwave irradiation for 45 min. Pd(PPh3)4 (0.100 g, 0.086 mmol) is added and the vial is heated again to 110 0C under microwave irradiation for 45 min. The mixture is then diluted with ethyl acetate and washed with water thrice. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica gel flash chromatography (dichloromethane-methanol, 19:1 ) to afford 6-chloro-2-(5-hydroxy-pyridin-3-yl)-indole-1- carboxylic acid tert-butyl ester as a solid. MS (ESI) m/z 345.06 (M+H)+

References: [1]Patent: WO2009/156462,2009,A2 .Location in patent: Page/Page column 162-163.

6
[ 352359-22-9 ]
[ 173999-05-8 ]
[ 1202552-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 85℃; for 1.0h;	A flask is charged with Λ/-(5-bromo-pyridin-3-ylmethyl)-methanesulfonamide (Example 163a, 530 mg, 2 mmol), Λ/-Boc-6-chloro-indole-2-boronic acid (525 mg, 3.0 mmol), s- Phos (41 mg, 0.10 mmol), finely crushed potassium phosphate (849 mg, 4.0 mmol) and toluene (20 ml_), and the mixture is degassed for 15 min. Pd2dba3 (37 mg, 0.04 mmol) is added and the mixture is stirred at 85 C for 1 h. The mixture is cooled to room temperature, diluted with DCM and silica gel (10 g) is added. The mixture is concentrated in vacuo and the residue is purified by silica gel flash chromatography eluting with a 0 to 90% ethyl acetate-heptane gradient to give 6-chloro-2-[5- (methanesulfonylamino-methyl)-pyridin-3-yl]-indole-1 -carboxylic acid tert-butyl ester. MS (ESI) m/z 436.1 and 437.9 (M+H)+.

References: [1]Patent: WO2009/156462,2009,A2 .Location in patent: Page/Page column 172.

7
[ 352359-22-9 ]
[ 402-49-3 ]
[ 1227625-76-4 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 2281 - 2283.

8
[ 330792-93-3 ]
[ 352359-22-9 ]
[ 1207731-33-6 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2264 - 2276.

9
[ 352359-22-9 ]
[ 1202551-93-6 ]

References: [1]Patent: WO2009/156462,2009,A2 .
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 9382 - 9394.
[3]Patent: CN104530000,2016,B .

10
[ 352359-22-9 ]
[ 1202550-44-4 ]

References: [1]Patent: WO2009/156462,2009,A2 .
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 9382 - 9394.

11
[ 352359-22-9 ]
[ 1202551-28-7 ]