Methyl 2-hydroxy-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)acetate → Methyl 2-hydroxy-2-[4-[8-(morpholin-4-yl)-2-[2-(quinolin-2-yl)ethyl]imidazo[1,2-a]pyrazin-5-yl]phenyl]acetate

HRID 1772604Notes

Reaction equation

HRID 1772604 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH2:12][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.[OH:29][CH:30]([C:35]1[CH:40]=[CH:39][C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][CH:36]=1)[C:31]([O:33][CH3:34])=[O:32]>>[OH:29][CH:30]([C:35]1[CH:36]=[CH:37][C:38]([C:2]2[N:7]3[CH:8]=[C:9]([CH2:11][CH2:12][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[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[N:4][CH:3]=2)=[CH:39][CH:40]=1)[C:31]([O:33][CH3:34])=[O:32]

Participants

3

Reactant 2

HCID 72221177Methyl 2-hydroxy-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)acetateHCID 1177278954-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

Product 1

HCID 117727871Methyl 2-hydroxy-2-[4-[8-(morpholin-4-yl)-2-[2-(quinolin-2-yl)ethyl]imidazo[1,2-a]pyrazin-5-yl]phenyl]acetateYield 75.4%

Procedure

Compound 3a (350 mg, 0.760 mmol) was subjected to Suzuki coupling conditions with methyl 2-hydroxy-2-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (666 mg, 2.28 mmol) using the reaction conditions described in Example 1, Step G to obtain compound 9c (300 mg, 72% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C30H29N5O4: 524.2 (M+H). Found 524.2.

Workup

  1. customthe reaction conditions

Sources & evidence

ORD record
ord-d2365da2aaeb42a286661a2e1dc963c9
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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