Isopropylamine → 2-Fluoro-6-iodo-3-[(isopropylamino)methyl]benzonitrile

HRID 239887Notes

Reaction equation

HRID 239887 reaction equation
[F:1][C:2]1[C:9]([CH:10]=O)=[CH:8][CH:7]=[C:6]([I:12])[C:3]=1[C:4]#[N:5].[CH:13]([NH2:16])([CH3:15])[CH3:14].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.CC(O)=O>[F:1][C:2]1[C:9]([CH2:10][NH:16][CH:13]([CH3:15])[CH3:14])=[CH:8][CH:7]=[C:6]([I:12])[C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 860193492-Fluoro-3-formyl-6-iodobenzonitrile

Product 1

HCID 666811522-Fluoro-6-iodo-3-[(isopropylamino)methyl]benzonitrileYield 32.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of Example 220A (1.00 g, 3.6 mmol) in MeOH (15 mL) was treated with isopropylamine (0.31 mL, 3.6 mmol) and sodium cyanoborohydride (227 mg, 3.6 mmol), and the mixture was stirred overnight at rt. HOAc (1 mL) was added and the reaction was stirred for 5 h, then treated with 1N NaOH and extracted with EtOAc. The extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography on silica gel eluting with 8% MeOH/CH2Cl2 to give the desired product (372 mg). MS (ESI(+)) m/e 318.9 (M+H)+.

Workup

  1. stirringthe reaction was stirred for 5 h
  2. extractionextracted with EtOAc
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 8% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-0c37f26836584f558828d193e79a1003
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Reaction notes

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