Carbon tetrabromide → 2-[N,N-bis(tert-Butoxycarbonyl)amino]-5-bromomethyl-3-methyl-pyridin

HRID 1789827Notes

Reaction equation

HRID 1789827 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[C:45]([CH3:46])=[CH:44][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[CH:44]=[C:45]([CH3:46])[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 220360372-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-3-methylpyridin

Product 1

HCID 220360092-[N,N-bis(tert-Butoxycarbonyl)amino]-5-bromomethyl-3-methyl-pyridinYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (7.43 g, 28.3 mmol) and CBr4 (9.49 g, 28.6 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-3-methylpyridin (8.00 g, 23.6 mmol) in dichloromethane (220 mL) at 0° C. The reaction mixture was stirred for 3 h and was then concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 80:20) gave 5-bromomethyl-2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methylpyridin (8.0 g,77%).

Workup

  1. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-56843a12b02b48b19d22edc5fd10549e
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

Loading…