Sodium Hydroxide → (5-(3,5-Difluorophenyl)furo[3,2-b]pyridin-3-yl)methanamine

HRID 2176652Notes

Reaction equation

HRID 2176652 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]3[C:15]([CH2:18][NH:19]C(=O)OC)=[CH:16][O:17][C:12]3=[CH:11][CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]3[C:15]([CH2:18][NH2:19])=[CH:16][O:17][C:12]3=[CH:11][CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57691037Methyl (5-(3,5-difluorophenyl)furo[3,2-b]pyridin-3-yl)methylcarbamate

Product 1

HCID 57691311(5-(3,5-Difluorophenyl)furo[3,2-b]pyridin-3-yl)methanamineYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask charged with methyl (5-(3,5-difluorophenyl)furo[3,2-b]pyridin-3-yl)methylcarbamate (680 mg, 2137 μmol) was added MeOH (20 mL), then aqueous NaOH (18 mL, 6 N, 106 mmol). The solution was heated at reflux for 60 h. The solution was concentrated to remove MeOH, then partitioned between CH2Cl2 (30 mL) and NaHCO3 (10 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (1×10 mL), then EtOAc (4×25 mL). The combined organic layers were concentrated to give a total of (5-(3,5-difluorophenyl)furo[3,2-b]pyridin-3-yl)methanamine (306.6 mg, 55% yield) as a brown foam. LRMS (ESI) m/z calcd for C14H11F2N2O (M+H) 261.1. found 261.2.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 60 h
  3. concentrationThe solution was concentrated
  4. customto remove MeOH
  5. custompartitioned between CH2Cl2 (30 mL) and NaHCO3 (10 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (1×10 mL)
  8. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-b13d023c61984bb691603b6723c8434a
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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