(R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate
• CAS No.: 143322-56-9
• Molecular Formula: C21H19BrN2O3
• Molecular Weight: 427.297
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID601138537
• Mol file: 143322-56-9.mol

Synonyms:143322-56-9;(R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate;R-3-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole;benzyl (2R)-2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate;(R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole;C21H19BrN2O3;SCHEMBL707001;DTXSID601138537;CS-M3330;benzyl (R)-2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate;MFCD09835149;(R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylate;AKOS015900097;CS-T-05889;(R)-(5-bromo-1H-indol-3-yl)[N-[(phenylmethoxy)carbonyl]-2-pyrrolidinyl]methanone;(R)-2-(5-Bromo-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester;AC-22723;CS-14991;C12951;3-(N- benzyloxycarbonyl-D-prolyl)-5-bromoindole;A808056;J-007800;(R)-3-(N-benzyloxycarbonyl-pyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole;(R)-3-(N-Benzyloxycarbonylpyrrolidin-2-yl-carbonyl)-5-bromo-1H-indole;(R)-3-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl )-5-bromo-1H-indole;(R)-Benzyl2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate;3-(1-BenzyIoxycarbonylpyrrolidin-2(R)-ylcarbonyl)-5-bromo-1H-indole;3-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylcarbonyl)-5-bromo-1H-indole;3-(N-Benzyloxycarbonyl-2(R)-pyrrolidinylcarbonyl)-5-bromo-1H-indole;benzyl (2R)-2-[(5-bromo-1H-indole-3-yl)carbonyl]pyrrolidine-1-carboxylate;(R)-2-(5-Bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylic acid benzyl ester;Phenylmethyl (2R)-2-[(5-bromo-1H-indol-3-yl)carbonyl]-1-pyrrolidinecarboxylate

Chemical Property of (R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.38E-14mmHg at 25°C
• Refractive Index: 1.678
• Boiling Point: 604.998 °C at 760 mmHg
• PKA: 14.40±0.30(Predicted)
• Flash Point: 319.692 °C
• PSA: 62.40000
• Density: 1.506 g/cm³
• LogP: 4.85220
• Storage Temp.: 2-8°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 426.05791
• Heavy Atom Count: 27
• Complexity: 552

Purity/Quality:

99% ^*data from raw suppliers

R-3-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C(=O)C3=CNC4=C3C=C(C=C4)Br
• Isomeric SMILES: C1C[C@@H](N(C1)C(=O)OCC2=CC=CC=C2)C(=O)C3=CNC4=C3C=C(C=C4)Br

Technology Process of (R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate

There total 7 articles about (R)-Benzyl 2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

5-bromo-1H-indole (10075-50-0) + N-benzyloxycarbonyl-D-proline acid chloride (61350-62-7) → (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-bromo-1H-indole (143322-56-9,331842-86-5)

Guidance literature:

5-bromo-1H-indole; With aluminum (III) chloride; In dichloromethane; at 0 - 5 ℃; for 1h;

N-benzyloxycarbonyl-D-proline acid chloride; In dichloromethane; at 0 - 5 ℃; for 6h; Reagent/catalyst; Concentration; Temperature; Solvent;

Reference yield: 72.0%

5-bromo-1H-indole (10075-50-0) + sodium hydrogencarbonate (144-55-8) + N-benzyloxycarbonyl-D-proline acid chloride (61350-62-7) → (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-bromo-1H-indole (143322-56-9,331842-86-5)

Guidance literature:

5-bromo-1H-indole; N-benzyloxycarbonyl-D-proline acid chloride; With tert-butylmagnesium chloride; In diethyl ether; at 0 - 20 ℃; for 0.75h;

sodium hydrogencarbonate; In diethyl ether; water; ethyl acetate;

Reference yield: 72.0%

→ (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-bromo-1H-indole (143322-56-9,331842-86-5)

Guidance literature:

upstream raw materials:

5-bromo-1H-indole

N-benzyloxycarbonyl-D-proline acid chloride

Z-D-proline

oxalyl dichloride

Downstream raw materials:

2-(5-thiophen-2-yl-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester

2-(5-thiophen-3-yl-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester

(R)-3-(N-Benzyloxycarbonylpyrrolidin-2-yl-methyl)-5-bromo-1H-indole

(R)-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole

Refernces

• 1、 -. "A preparation method of the midbody according to sets up Qu Tan". Paragraph 0031; 0032; 0033; 0034; 0035; 0036-0044. . Retrieved 2017/06/30.
• 2、 -. "SYNTHESIS OF 3--5-[2-(PHENYLSULFONYL)ETHYL]-1H-INDOLE". Page/Page column 4. . Retrieved 2011/07/29.