Sodium Carbonate → HCID 136373242, compound

HRID 1014732Notes

Reaction equation

HRID 1014732 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[N:14]([CH2:18][CH:19]4[CH2:23][CH2:22][CH2:21][N:20]4C(OC(C)(C)C)=O)[C:15](=[O:17])[NH:16][C:11]3=[N:10][CH:9]=2)=[CH:4][CH:3]=1.BrC1N=C2N(CC3CCCN3C(OC(C)(C)C)=O)C(=O)NC2=NC=1.OC1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]3[N:14]([CH2:18][CH:19]4[CH2:23][CH2:22][CH2:21][NH:20]4)[C:15](=[O:17])[NH:16][C:11]3=[N:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 86626413HCID 86626413, compoundHCID 136414662HCID 136414662, compound

Product 1

HCID 136373242HCID 136373242, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-((6-(4-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)methyl)pyrrolidine-1-carboxylate, tert-Butyl 2-((6-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)methyl)pyrrolidine-1-carboxylate (0.5 g., 1.25 mmol), 4-hydroxyphenylboronic acid (0.17 g., 1.25 mmol), dichloro[1,1′-bis(diphenylphosphino) ferrocene]palladium(II) dichloromethane adduct (0.103 g. 0.126 mmol) and sodium carbonate (0.665 g., 6.28 mmol) were reacted for 40 min in 1,4-dioxane (4 mL) according to General Procedure B2 and purified using silica gel chromatography (60% ethyl acetate in hexanes) to afford the title compound (0.21 g, 41.4% yield). MS (ESI) m/z 412.4 [M+1]+.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-c39da7e9cbb04f02bcabd245ecb5bd98
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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