Cyclopropylboronic acid → 6-(4-Chloro-phenyl)-8-cyclopropyl-imidazo[1,2-a]pyridine

HRID 558627Notes

Reaction equation

HRID 558627 reaction equation
Br[C:2]1[C:3]2[N:4]([CH:15]=[CH:16][N:17]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH:7]=1.[CH:18]1(B(O)O)[CH2:20][CH2:19]1>>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:7]=[C:2]([CH:18]3[CH2:20][CH2:19]3)[C:3]3[N:4]([CH:15]=[CH:16][N:17]=3)[CH:5]=2)=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 2760897Cyclopropylboronic acidHCID 670008688-Bromo-6-(4-chloro-phenyl)-imidazo[1,2-a]pyridine

Product 1

HCID 670008386-(4-Chloro-phenyl)-8-cyclopropyl-imidazo[1,2-a]pyridineYield 59.2%

Procedure

Prepared from 8-bromo-6-(4-chloro-phenyl)-imidazo[1,2-a]pyridine (example C.27 step 3) (6.15 g, 20 mmol) and cyclopropylboronic acid (2.23 g, 26 mmol) as described in example C.25 step 4. Obtained the title compound as an orange solid (3.18 g, 59%; 88% pure, contains 12% 8-cyclopropyl-6-(4-cyclopropyl-phenyl)-imidazo[1,2-a]pyridine). MS (ISP) 269.3 [(M+H)+], 271.3 [(M+2+H)+].

Sources & evidence

ORD record
ord-b87962bfb26d40079e8156b7f277ded8
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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