Carbon tetrabromide → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromomethyl-4-methyl-pyridin

HRID 1789836Notes

Reaction equation

HRID 1789836 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[C:25]([O:29][C:30]([N:32]([C:40]1[CH:45]=[C:44]([CH3:46])[C:43](CO)=[CH:42][N:41]=1)[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:31])([CH3:28])([CH3:27])[CH3:26]>ClCCl>[Br:24][CH2:20][C:43]1[C:44]([CH3:46])=[CH:45][C:40]([N:32]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])=[N:41][CH:42]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 220360382-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-4-methylpyridin

Product 1

HCID 220360082-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromomethyl-4-methyl-pyridinYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (4.69 g, 17.9 mmol) and CBr4 (4.89 g, 14.8 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-4-methylpyridin (5.00 g, 22.0 mmol) in dichloromethane (130 mL) at 0° C. The reaction mixture was stirred for 3 h and was then diluted with dichloromethane. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 80:20) gave 5-bromomethyl-2-[N,N-bis(tert-butoxycarbonyl)amino]-4-methylpyridin (5.35 g, 90%).

Workup

  1. washThe organic phase was washed with water
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb5aa5ebdc914155b2566bb3679d71a8
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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