tert-Butyl carbamate → 2-(Tert-butoxycarbonylamino)-6-chloroisonicotinic acid

HRID 148

Reaction equation

HRID 148 reaction equation
CC(C)(C)OC(N)=O.O=C(O)c1cc(Cl)nc(Cl)c1>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Pd].[Pd]>CC(C)(C)OC(=O)Nc1cc(C(=O)O)cc(Cl)n1

Participants

7

Reactant 2

HCID 77922tert-Butyl carbamateHCID 948302,6-Dichloroisonicotinic acid

Product 1

HCID 722120522-(Tert-butoxycarbonylamino)-6-chloroisonicotinic acidYield 0%

Reagents, catalysts & solvents 4

HCID 62657Potassium Phosphate, TribasicReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Reagents were mixed in a 25 mL round bottom flask and flushed well with nitrogen - heated at 100 °C for 16 h. The mixture looked dark black. Could not detect any starting material or product! It was discarded.

Sources & evidence

ORD record
ord-7c9ead47a3324fac997f2b8af6afca02
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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