Di-tert-butyl dicarbonate → tert-butyl N-[3-(1,3-benzoxazol-2-yl)-5-bromo-2-pyridyl]-N-tert-butoxycarbonyl-carbamate

HRID 908400Notes

Reaction equation

HRID 908400 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([N:25]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[N:12][CH:13]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:15]=1.O1C2C=CC=CC=2N=C1C1C(N)=NC=C([Br:55])C=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CN(C)C1C=CN=CC=1.CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([N:25]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[N:12][CH:13]=[C:14]([Br:55])[CH:15]=1

Participants

6

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 673880093-(Benzoxazol-2-yl)-5-bromo-pyridin-2-amineHCID 67388208Tert-butyl N-[3-(1,3-benzoxazol-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate

Product 1

HCID 67388003tert-butyl N-[3-(1,3-benzoxazol-2-yl)-5-bromo-2-pyridyl]-N-tert-butoxycarbonyl-carbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

The tert-butyl N-[3-(1,3-benzoxazol-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate used as starting material was prepared as follows: N,N-dimethylpyridin-4-amine (42.1 mg) was added to 3-(1,3-benzoxazol-2-yl)-5-bromo-pyridin-2-amine (500 mg) and di-tert-butyl dicarbonate (1.069 g) suspended in DMF (5 ml). The resulting mixture was stirred at 25° C. for 48 hours. The reaction mixture was quenched with a saturated aqueous solution of sodium hydrogencarbonate (15 ml). The resulting precipitate was collected by filtration, washed with water and dried. The crude was taken up into ethyl acetate and filtered through a pad of silica gel. The resulting filtrate was concentrated to afford tert-butyl N-[3-(1,3-benzoxazol-2-yl)-5-bromo-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (710 mg) as a solid. NMR Spectrum: (CDCl3): 1.32 (s, 18H), 7.37-7.44 (m, 2H), 7.60 (dd, 1H), 7.80 (dd, 1H), 8.70 (d, 1H), 8.81 (d, 1H); Mass spectrum: M+H+ 491;

Workup

  1. customwas prepared
  2. customThe reaction mixture was quenched with a saturated aqueous solution of sodium hydrogencarbonate (15 ml)
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried
  6. filtrationfiltered through a pad of silica gel
  7. concentrationThe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-98a52cc0a1264b3fa54f8dad7fb2697d
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

Loading…