Dichloromethane → HCID 67457433, compound

HRID 639707Notes

Reaction equation

HRID 639707 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[N:5]([C:14]1[CH:19]=[C:18](Cl)[N:17]=[C:16]([NH2:21])[C:15]=1[N+:22]([O-:24])=[O:23])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[CH3:2].[CH:26]([B-](F)(F)F)=[CH2:27].[K+].C(Cl)Cl.C(N(CC)CC)C>CC(O)C.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]>[CH2:1]([O:3][C:4](=[O:25])[N:5]([C:14]1[CH:19]=[C:18]([CH:26]=[CH2:27])[N:17]=[C:16]([NH2:21])[C:15]=1[N+:22]([O-:24])=[O:23])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 57856581HCID 57856581, compound

Product 1

HCID 67457433HCID 67457433, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

(2-Amino-6-chloro-3-nitro-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester (715 mgs/1.955 mmols), potassium vinyltrifluoroborate (415 mgs/3.098 mmols), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II).CH2Cl2 (90 mgs/0.11 mmols) and triethylamine (0.28 mls/2.0 mmols) were combined in iPrOH (8.0 mls) and heated at 50° C. under N2 for 24 hrs. Preadsorbed directly onto silica and purified by column chromatography to give title compound (270 mgs) as a purple resin

Workup

  1. customPreadsorbed directly onto silica and purified by column chromatography

Sources & evidence

ORD record
ord-e731ae9ecacf4dd89e022e2e10419e16
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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