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

HRID 40357Notes

Reaction equation

HRID 40357 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-5fb4aacd58a74f9b9fb55a95ffbca385
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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