1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-(1,1-diMethylethyl)-5-Methyl- synthesis

4synthesis methods

Product Name:1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-(1,1-diMethylethyl)-5-Methyl-
CAS Number:1187448-81-2
Molecular formula:C12H15ClN2
Molecular Weight:222.71

1H-Pyrrolo[2,3-b]pyridine, 2-(1,1-dimethylethyl)-5-methyl-, 7-oxide

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1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-(1,1-diMethylethyl)-5-Methyl-

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Yield:-

Reaction Conditions:

Stage #1: 2-(1,1-dimethylethyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine 7-oxidewith methanesulfonyl chloride in N,N-dimethyl-formamide at 50; for 1.25 h;
Stage #2: with sodium hydroxide in water;N,N-dimethyl-formamide;

Steps:

3

Description 3 (D3); 4-chloro-2-(1 ,1 -dimethylethyl)-5-methyl-1W-pyrrolo[2,3-b]pyridine; 2-(1 ,1-Dimethylethyl)-5-methyl-1 H-pyrrolo[2,3-5]py?dine 7-oxide (D2) (3.8g) was suspended in DMF(20ml) and heated to 5O⁰C. The mixture was treated dropwise with methane sulphonyl chloride (7ml) over 15 minutes. The reaction was heated at 50⁰C for an hour.The reaction was poured into water (150ml) and neutralised with 10M-NaOH. The yellow precipitate was collected and dried in a flow of air. 3.35g (4:1 mixture of product and 2-(1 ,1-dimethylethyl)-5-methyl-1 H-pyrrolo[2,3-6]pyridine)LCMS (method B): MH+ 223 seen at retention time: 1.33 minutes.

References:

WO2009/112473,2009,A1 Location in patent:Page/Page column 62

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References

630-18-2 Synthesis

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References

2-(tert-butyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine

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References