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

HRID 1293736Notes

Reaction equation

HRID 1293736 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-e572b9bad0cb44229454dc1ffed04fb4
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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