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Home > Encyclopedia > 1-BOC-5-chloroindole-3-boronic acid, pinacol ester

1-BOC-5-chloroindole-3-boronic acid, pinacol ester

1-BOC-5-chloroindole-3-boronic acid, pinacol ester structure

1-BOC-5-chloroindole-3-boronic acid, pinacol ester 

structure
  • CAS No:

    1218790-30-7

  • Formula:

    C19H27BClNO5

  • Chemical Name:

    1-BOC-5-chloroindole-3-boronic acid, pinacol ester

  • Synonyms:

    tert-Butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate;1-Boc-5-chloroindole-3-boronic acidpinacol ester;1-BOC-5-chloroindole-3-boronic acid, pinacol ester;tert-butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate;1H-Indole-1-carboxylic acid, 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester;CTK8B6488;DTXSID80682308;ANW-53531;AKOS015999329;ZINC169746302

1-BOC-5-chloroindole-3-boronic acid, pinacol ester Basic Attributes

396

377.15700

DTXSID80682308

2934999090

Characteristics

49.7

4.37710

1-BOC-5-chloroindole-3-boronic acid, pinacol ester Use and Manufacturing

Pd(dppf)Cl2 (29 mg, 0.04 mmol, 3 molpercent) and tert-butyl 5-chloro-3-iodo-1H-indole-1-carboxylate 10 (500 mg, 1.32 mmol) were placed in a dry screwcapvessel with a septum. Then, dry toluene (6.5 mL) was added, and the mixture was degassed with argon (5 min). Dry triethylamine(0.7 mL) and 4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane(0.3 mL, 2 mmol) were successively added to the mixture, whichwas then stirred at 80 C (preheated oil bath) for 3 h (monitoredby TLC). Subsequently the mixture was cooled to room temperatureand filtered through Celite. The filtrate was concentratedand the residue was purified by flash chromatography (eluent;hexane/ethyl acetate = 10/1) to obtain 418 mg of 11 (totalyield = 84percent). Characterization was in agreement with literaturedata.33, 34 1H NMR (500 MHz, CDCl3) d 8.08 (d, J = 8.8 Hz, 1H), 8.00(s, 1H), 7.95 (d, J = 2.1 Hz, 1H), 7.26 (dd, J = 8.8, 2.1 Hz, 1H), 1.65(s, 9H), 1.38 (s, 12H).

Computed Properties

Molecular Weight:377.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:377.1565161
Monoisotopic Mass:377.1565161
Topological Polar Surface Area:49.7
Heavy Atom Count:26
Complexity:546
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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