HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Methyl 3-Amino-6-bromopyrazine-2-carboxylate → HCID 68529012, compound

HRID 736603
Notes
Print preview

Reaction equation

HRID 736603 reaction equation
[N:1]1([S:6]([C:9]2[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:18][C:19]1[C:20]([C:26]([O:28][CH3:29])=[O:27])=[N:21][C:22](Br)=[CH:23][N:24]=1>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:18][C:19]1[C:20]([C:26]([O:28][CH3:29])=[O:27])=[N:21][C:22]([C:12]2[CH:13]=[CH:14][C:9]([S:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)(=[O:8])=[O:7])=[CH:10][CH:11]=2)=[CH:23][N:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 10400111[4-(Pyrrolidine-1-sulfonyl)phenyl]boronic acid

Product 1

HCID 68529012HCID 68529012, compoundYield 245.3%

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst
HCID 18180031
Water 1,2-dimethoxyethane
Solvent

Conditions

Temperature
160 °C

Procedure

4-(Pyrrolidin-1-ylsulfonyl)phenylboronic acid (0.33 g, 1.29 mmol), methyl 3-amino-6-bromopyrazine-2-carboxylate (0.25 g, 1.08 mmol; described in: H. Ellingson, J. Amer. Chem. Soc. 1949, 2798), K3PO3 (3 M, 1.1 mL, 3.2 mmol), and Pd(dppf)Cl2 (0.044 g, 54 μmol) were suspended in ethylene glycol dimethyl ether/water (1.5:0.5 mL) and heated in a microwave oven at 160° C. for 10 min. The reaction was repeated 3 times. The combined product mixtures were evaporated with silica gel and the crude product was purified by chromatography on silica gel using a heptane to ethyl acetate gradient to give 0.96 g (82% yield) of the title compound: MS (ES) m/z 363 (M++1).

Workup

  1. customThe combined product mixtures were evaporated with silica gel
  2. customthe crude product was purified by chromatography on silica gel using a heptane to ethyl acetate gradient

Sources & evidence

ORD record
ord-619a809a2275423a84294bc8a7b6fc77
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07595319B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes