(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine → (E)-Ethyl 1-(4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)phenyl)piperidine-4-carboxylate

HRID 1772628Notes

Reaction equation

HRID 1772628 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.CC1(C)OB([C:35]2[CH:40]=[CH:39][C:38]([N:41]3[CH2:46][CH2:45][CH:44]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:43][CH2:42]3)=[CH:37][CH:36]=2)OC1(C)C>>[O:26]1[CH2:27][CH2:28][N:23]([C:5]2[C:6]3[N:7]([CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=3)[C:2]([C:35]3[CH:36]=[CH:37][C:38]([N:41]4[CH2:46][CH2:45][CH:44]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:43][CH2:42]4)=[CH:39][CH:40]=3)=[CH:3][N:4]=2)[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 117728505(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholineHCID 131734180Ethyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-4-carboxylate

Product 1

HCID 86345485(E)-Ethyl 1-(4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)phenyl)piperidine-4-carboxylateYield 44.7%

Procedure

Compound 2b (350 mg, 0.760 mmol) was subjected to Suzuki coupling conditions with ethyl 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperidine-4-carboxylate (881 mg, 2.28 mmol) using the reaction conditions described in Example 1, Step G to obtain compound 18d as a brown solid (200 mg, 42% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C35H36N6O3: 589.3 (M+H). Found 589.2.

Workup

  1. customthe reaction conditions

Sources & evidence

ORD record
ord-c7537fbfece7456eb8960221ce7f4ced
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…