Ethane, 2-bromo-1,1-diethoxy- → 6-Bromo-8-fluoroimidazo[1,2-a]pyridine

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([F:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10](OC(OCC)CBr)[CH3:11]>>[Br:1][C:2]1[CH:3]=[C:4]([F:9])[C:5]2[N:6]([CH:10]=[CH:11][N:8]=2)[CH:7]=1

Participants

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-

HCID 508511302-Amino-5-bromo-3-fluoropyridine

Product 1

HCID 220319336-Bromo-8-fluoroimidazo[1,2-a]pyridineYield 89%

Procedure

Prepared from 5-bromo-3-fluoro-pyridin-2-ylamine (example C.29 step 3) (3.1 g, 15.7 mmol) and bromoacetaldehyde diethyl acetal (90%, 4.86 mL, 31.3 mmol) as described in example C.20 step 1. Obtained the title compound as a light brown solid (3.0 g, 89%). MS (ISP) 215.1 [(M+H)+], 217.1 [(M+2+H)+].

Sources & evidence

ORD record: ord-6abd51c06bb64459a76818b26f05e4f6
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446113B2

Reaction notes

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