tert-butyl N-(5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate → (E)-tert-Butyl5-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-ylcarbamate

HRID 1772614Notes

Reaction equation

HRID 1772614 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)C(C)(C)OB([C:37]2[CH:38]=[CH:39][C:40]([NH:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[N:41][CH:42]=2)O1>>[C:46]([O:45][C:44](=[O:50])[NH:43][C:40]1[CH:39]=[CH:38][C:37]([C:2]2[N:7]3[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]=[C:6]3[C:5]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[N:4][CH:3]=2)=[CH:42][N:41]=1)([CH3:49])([CH3:47])[CH3:48]

Participants

3

Reactant 2

HCID 17750222tert-butyl N-(5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamateHCID 117728505(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

Product 1

HCID 117732264(E)-tert-Butyl5-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-ylcarbamateYield 48%

Procedure

Compound 2b (500 mg, 1.15 mmol) was subjected to Suzuki coupling conditions with tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-ylcarbamate using the reaction conditions described in Example 1, Step G to obtain compound 13a as a yellow solid (300 mg, 48% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C31H31N7O3: 550.2 (M+H). Found 550.2.

Workup

  1. customthe reaction conditions

Sources & evidence

ORD record
ord-547c5462f06e4a2f9a6e6aced84958dd
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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