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

HRID 269065Notes

Reaction equation

HRID 269065 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-8e81bc209c0449698c9d19d754159802
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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