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

HRID 2237928Notes

Reaction equation

HRID 2237928 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-70c58769eeb443c9bbb6e2194f3dcac0
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

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