2-Aminopyridine → 4-Tert-butyl-phenyl-imidazo[1,2-a]pyridine

HRID 729487Notes

Reaction equation

HRID 729487 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[C:15](N4CCNCC4)[N:14]3[CH:25]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].NC1C=CC=CN=1.C(C1C=CC(C(=O)CCl)=CC=1)(C)(C)C>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]3[CH:25]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 104392-AminopyridineHCID 2296611-(4-Tert-butylphenyl)-2-chloroethan-1-oneHCID 57832787HCID 57832787, compound

Product 1

HCID 578327904-Tert-butyl-phenyl-imidazo[1,2-a]pyridine

Procedure

Scheme 4 provides the synthesis of a specific intermediate following the general procedures set forth in Scheme 3, which can be further elaborated to provide compounds of the Formula (IB). 2-(4-tert-Butyl-phenyl)-5-piperazin-1-yl-imidazo[1,2-a]pyridine (7) was obtained as described in Scheme 4. 2-Aminopyridine was cyclized with 4-tert-butylphenacyl chloride to afford 2-(4-tert-butyl-phenyl-imidazo[1,2-a]pyridine (5). Lithiation followed by bromination provided a ratio of three products (6a, 70.7%; 6b, 12.3%; and 6c, 17.0%). Heating the mixture with piperazine provided (7) from (6a), which was easily separated from unreactive (6b) and (6c).

Workup

  1. customScheme 4 provides
  2. customthe synthesis of a specific intermediate
  3. customto provide compounds of the Formula (IB)

Sources & evidence

ORD record
ord-72dd2b5fca3a4e00a069922de2848e6b
Source dataset
uspto-grants-2009_09
Patent number
US07582636B2

Reaction notes

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