Dimethylformamide → HCID 86647427, compound

HRID 2071053Notes

Reaction equation

HRID 2071053 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[N:6][CH:7]=1.[CH3:17][N:18](C=O)C>CCOCC.[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]([C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[N:6][CH:7]=1)#[N:18]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 467392903-(N-BOC-aminomethyl)-5-bromopyridine

Product 1

HCID 86647427HCID 86647427, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

To tert-butyl (5-bromopyridin-3-yl)methylcarbamate (384 mg, 1.34 mmol) in DMF (10 ml), Zn(CN)2 (94 mg, 0.80 mmol) and Pd(PPh3)4 were added and heated at 110° C. for 3 h. Then the reaction mixture was cooled to RT, diluted with ether, washed with ammonium hydroxide solution, water and brine. Crude residue was column chromatographed (40% ethylacetate/60% Hexanes) to yield tert-butyl (5-cyanopyridin-3-yl)methylcarbamate in 86% yield.

Workup

  1. temperatureThen the reaction mixture was cooled to RT
  2. washwashed with ammonium hydroxide solution, water and brine
  3. customchromatographed (40% ethylacetate/60% Hexanes)

Sources & evidence

ORD record
ord-ae46e02925904f5d80074ae9b8aaca1b
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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