Binap, (A+-)- → tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}(pentyloxy)carbamate

HRID 1258571Notes

Reaction equation

HRID 1258571 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]2[N:22]([CH3:23])[N:21]=[N:20][N:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1.[C:24]([O:28][C:29](=[O:37])[NH:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])([CH3:27])([CH3:26])[CH3:25].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(O[K])(C)(C)C>C1(C)C=CC=CC=1>[CH3:23][N:22]1[C:18]([C:11](=[N:10][O:9][CH2:8][C:6]2[N:7]=[C:2]([N:30]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:29](=[O:37])[O:28][C:24]([CH3:25])([CH3:26])[CH3:27])[CH:3]=[CH:4][CH:5]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:19][N:20]=[N:21]1

Participants

6

Reactant 4

HCID 634876Binap, (A+-)-HCID 86653112N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimineHCID 86653126Tert-butyl (pentyloxy)carbamateHCID 178418922HCID 178418922, compound

Product 1

HCID 86653127tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}(pentyloxy)carbamateYield 43.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

In a purged and dried vessel, N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.2 g, 0.536 mmol, 1 eq.) was dissolved in 3 ml of toluene and tert-butyl(pentyloxy)carbamate (0.217 g, 1.072 mmol 2 eq.) was added followed by Pddba2 (0.065 g, 0.113 mmol, 0.21 eq.) and BINAP (0.069 g, 0.113 mmol, 0.21 eq.). Then tBuOK (0.12 g, 1.07 mmol, 2 eq.) was added and the vessel purged with argon and sealed. The reaction was stirred at 90° C. for 24 h. The solvent was evaporated and residue taken in EtOAc, filtered through “celite”, washed with H2O, dried over MgSO4, and concentrated. The crude was purified by chromatography on silica gel to give tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}(pentyloxy)carbamate (0.115 g, 41%) as a viscous yellow oil.

Workup

  1. customIn a purged
  2. customdried vessel
  3. customthe vessel purged with argon
  4. customsealed
  5. customThe solvent was evaporated
  6. filtrationfiltered through “celite”
  7. washwashed with H2O
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe crude was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ea1197370c7946a39f5806971d8c2027
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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