Methanol → HCID 67453740, compound

HRID 1474101Notes

Reaction equation

HRID 1474101 reaction equation
[F:1][CH:2]([F:17])[O:3][C:4]1[N:9]=[C:8]([C:10]([NH:13]C(=O)[O-])([CH3:12])[CH3:11])[CH:7]=[CH:6][CH:5]=1.[Si](I)(C)(C)C.CO.O>C(#N)C>[F:17][CH:2]([F:1])[O:3][C:4]1[N:9]=[C:8]([C:10]([NH2:13])([CH3:11])[CH3:12])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 85247Trimethylsilyl iodideHCID 86684827HCID 86684827, compound

Product 1

HCID 67453740HCID 67453740, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(6-(difluoromethoxy)pyridin-2-yl)propan-2-ylcarbamate (12.4 g, 48 mmol) in acetonitrile (50 mL) was added TMSI (10 mL). The reaction was stirred 30 min and then poured into methanol (100 mL) and water (5 mL). The mixture was concentrated, dissolved in ethyl acetate (200 mL), and then washed with 1N NaOH (2×30 mL). The organic layer was separated, dried over Na2SO4, concentrated, and chromatographed with silica gel (50% EtOAc/hex, then 5-20% MeOH/CH2Cl2) to afford 2-(6-(difluoromethoxy)pyridin-2-yl)propan-2-amine (8.8 g, 92%) as a yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (200 mL)
  3. washwashed with 1N NaOH (2×30 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customchromatographed with silica gel (50% EtOAc/hex

Sources & evidence

ORD record
ord-b97a5103cda046d08666d17bfa99183c
Source dataset
uspto-grants-2015_04
Patent number
US09018223B2

Reaction notes

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