tert-Butyl carbamate → HCID 58337569, compound

HRID 1887440Notes

Reaction equation

HRID 1887440 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[O:5][C:6]1[CH:7]=[N:8][CH:9]=[N:10][CH:11]=1.[C:16](=[O:23])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[NH2:17].CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>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.C(Cl)(Cl)Cl.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:15][C:13]1[CH:14]=[C:2]([NH:17][C:16](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:3]=[C:4]([O:5][C:6]2[CH:7]=[N:8][CH:9]=[N:10][CH:11]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 77922tert-Butyl carbamateHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 23676156Sodium t-butoxideHCID 58337657HCID 58337657, compound

Product 1

HCID 58337569HCID 58337569, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 1140TolueneSolvent

Procedure

Compound 7 (50 mg, 0.17 mmol, 1.0 eq), tert-butyl carbamate (25 mg, 0.21 mmol, 1.2 eq), sodium tert-butoxide (24 mg, 0.25 mmol, 1.4 eq), Tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (5.4 mg, 0.0052 mmol, 0.030 eq), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (8 mg, 0.02 mmol, 0.09 eq) and toluene (0.65 mL) were added to a round-bottom flask, purged with argon and stirred at room temperature overnight. The reaction was filtered over a plug of celite and the plug was washed with 5% MeOH/CH2Cl2. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 41 mg (73%) of the title compound as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 9.05 (s, 1H), 8.55 (s, 2H), 7.26 (s, 1H), 7.18 (s, 1H), 6.90 (s, 1H), 6.73 (t, J=1.9 Hz, 1H), 1.54 (s, 9H); ES-MS [M+1]+: 322.1.

Workup

  1. custompurged with argon
  2. filtrationThe reaction was filtered over a plug of celite
  3. washthe plug was washed with 5% MeOH/CH2Cl2
  4. customThe solvents were removed in vacuo
  5. customthe crude mixture was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-095a8b8ccf4148189646c3b63326fffd
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

Loading…