O,O-Dipyridin-2-yl carbonothioate → 4-(isothiocyanatomethyl)-1H-pyrrolo[2,3-b]pyridine

HRID 706346Notes

Reaction equation

HRID 706346 reaction equation
[C:1](=[S:16])(OC1C=CC=CN=1)OC1C=CC=CN=1.[NH:17]1[C:21]2=[N:22][CH:23]=[CH:24][C:25]([CH2:26][NH2:27])=[C:20]2[CH:19]=[CH:18]1>O1CCCC1>[N:27]([CH2:26][C:25]1[CH:24]=[CH:23][N:22]=[C:21]2[NH:17][CH:18]=[CH:19][C:20]=12)=[C:1]=[S:16]

Participants

4

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 11679841(1H-Pyrrolo[2,3-b]pyridin-4-yl)methanamine

Product 1

HCID 895249914-(isothiocyanatomethyl)-1H-pyrrolo[2,3-b]pyridineYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

O,O-di-2-pyridinyl thiocarbonate (1136 mg, 4.89 mmol) was added to a solution of (1H-pyrrolo[2,3-b]pyridin-4-yl)methanamine (720 mg, 4.89 mmol) in tetrahydrofuran (THF) (60 mL). Let stir at RT for 30 minutes and concentrated. The residue was purified via Biotage (0% to 50% gradient EtOAc:Hex; 25 g-HP-silica gel column) to obtain 690 mg of 4-(isothiocyanatomethyl)-1H-pyrrolo[2,3-b]pyridine. 1H NMR (400 MHz, DMSO-d6) δ ppm 5.26 (s, 2H) 6.57 (dd, J=3.54, 1.77 Hz, 1H) 7.07 (d, J=4.80 Hz, 1H) 7.50-7.63 (m, 1H) 8.26 (d, J=4.80 Hz, 1H) 11.86 (br. s., 1H); MS[MH]+=190.0

Workup

  1. concentrationconcentrated
  2. customThe residue was purified via Biotage (0% to 50% gradient EtOAc:Hex; 25 g-HP-silica gel column)

Sources & evidence

ORD record
ord-49a93914f6254992843199a35b5c19a5
Source dataset
uspto-grants-2015_11
Patent number
US09174984B2

Reaction notes

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