Nitrogen → N-tert-Butyl-3-methylpyridin-2-amine

HRID 334844Notes

Reaction equation

N#N.Br[C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][N:5]=1.CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:63]([NH2:67])([CH3:66])([CH3:65])[CH3:64]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:63]([NH:67][C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:66])([CH3:65])[CH3:64]

Participants

Conditions

Temperature: 70 °C

Procedure

To a 3 or 4-necked flask (100 L) with water cooling condenser, mechanical stirring and N2 was charged toluene (40 L), 2-bromo-3-methylpyridine (4.966 kg), sodium t-butoxide (5.60 kg). The slurry was then sparged N2 for 10 min; then tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, 0.065 kg, 0.071 mol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 0.106 kg, 0.171 mol) and t-butylamine (4.51 L) were charged. The resulting dark mixture was stirred 10 min at 23° C. under N2 and then heated to 70° C. (internal temp) with a steam bath. No t-butyl amine reflux was noticed.

Workup

stirringThe resulting dark mixture was stirred 10 min at 23° C. under N2

Sources & evidence

ORD record: ord-be17da8ff4004953a06e5724403a62b6
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883807B2

Reaction notes

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