2-Chloropyridine → Tert-butyl 2-pyridin-2-ylpyrrole-1-carboxylate

HRID 439278Notes

Reaction equation

HRID 439278 reaction equation
CC(C)(C)OC(=O)n1cccc1B(O)O.Clc1ccccn1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC2=NCCCN2CC1.C1CCOC1.CS(=O)(=O)[O][Pd][c]1ccccc1-c1ccccc1N.O>CC(C)(C)OC(=O)n1cccc1-c1ccccn1

Participants

10

Reactant 2

HCID 79772-ChloropyridineHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid

Product 1

HCID 86058205Tert-butyl 2-pyridin-2-ylpyrrole-1-carboxylateYield 48.4%

Reagents, catalysts & solvents 7

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneReagentHCID 178420537HCID 178420537, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent5×HCID 180AcetoneWorkupHCID 931NaphthaleneInternal standardHCID 962WaterWorkup

Conditions

Temperature
108.5 °C

Workup

  1. additionAs soon as the slug leaves the reactor and is detected at PS2,a quench solution volume equal to the reaction slug volume(prepared slug volume + base injection volume) is injected into the reaction slug

Sources & evidence

ORD record
ord-912c0bbddf424b31a7529ad21744cdd9
Source dataset
Reizman Suzuki Cross-Coupling
Original link
View source

Reaction notes

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