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1083181-26-3

1083181-26-3 Structure

1083181-26-3 Structure
IdentificationBack Directory
[Name]

3-iodo-1H-pyrrolo[3,2-b]pyridine
[CAS]

1083181-26-3
[Synonyms]

3-Iodo-4-azaindole
3-iodo-1H-pyrrolo[3,2-b]pyridine
1H-Pyrrolo[3,2-b]pyridine, 3-iodo-
[Molecular Formula]

C7H5IN2
[MDL Number]

MFCD11559019
[MOL File]

1083181-26-3.mol
[Molecular Weight]

244.03
Chemical PropertiesBack Directory
[Boiling point ]

360.7±22.0 °C(Predicted)
[density ]

2.082
[storage temp. ]

2-8°C(protect from light)
[pka]

13.16±0.40(Predicted)
[Appearance]

White to off-white Solid
[InChI]

InChI=1S/C7H5IN2/c8-5-4-10-6-2-1-3-9-7(5)6/h1-4,10H
[InChIKey]

ZLVQSDNBINQPHB-UHFFFAOYSA-N
[SMILES]

C12C(I)=CNC1=CC=CN=2
Questions And AnswerBack Directory
[Uses]

3-Iodo-1H-pyrrolo[3,2-B]pyridine is a pyridine derivative that can be used to prepare plasma kallikrein inhibitors.
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H319-H335-H302+H312+H332-H315
[Precautionary statements ]

P301+P312-P302+P352-P305+P351+P338
[HS Code ]

2933998090
Spectrum DetailBack Directory
[Spectrum Detail]

3-iodo-1H-pyrrolo[3,2-b]pyridine(1083181-26-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

4-Azaindole

272-49-1

3-iodo-1H-pyrrolo[3,2-b]pyridine

1083181-26-3

1H-pyrrolo[3,2-b]pyridine (1.94 g, 16.4 mmol) was used as starting material and dissolved in tetrahydrofuran (THF, 10 mL). Subsequently, N-iodosuccinimide (NIS, 4.06 g, 18.1 mmol) was added to this solution. The reaction mixture was stirred at room temperature overnight, during which precipitation was observed to be generated. Upon completion of the reaction, the precipitate was collected by filtration and washed sequentially with a small amount of THF and heptane. The resulting white solid was dried under vacuum to afford the target product 3-iodo-1H-pyrrolo[3,2-b]pyridine (4.1 g, quantitative yield). The structure of the product was confirmed by 1H NMR (DMSO-d6, 300 MHz) δ 8.40 (s, 1H), 7.90-7.70 (m, 2H), 7.15 (d, 1H) and LC-MS (retention time 0.41 min; m/z 245 [M+1]+).

[References]

[1] Patent: WO2011/78984, 2011, A1. Location in patent: Page/Page column 72
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 24, p. 6935 - 6938
[3] Patent: WO2018/11628, 2018, A1. Location in patent: Paragraph 00203
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 14, p. 5129 - 5136
[5] Patent: US2015/94328, 2015, A1. Location in patent: Paragraph 0349; 0350-0352
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