Tetrahydrofuran → HCID 67980879, compound

HRID 1427433Notes

Reaction equation

HRID 1427433 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.O1CCCC1.[CH2:25]([Mg]Br)[CH:26]([CH3:28])[CH3:27].[BH4-].[Na+]>CO>[CH3:25][CH:26]([CH3:28])[CH2:27][CH:8]([C:6]1[CH:5]=[CH:4][C:3]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=2)=[C:2]([CH3:1])[CH:7]=1)[NH2:9]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 67981173HCID 67981173, compoundHCID 178418816HCID 178418816, compound

Product 1

HCID 67980879HCID 67980879, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A microwave reaction vial was charged with 2-methyl-4′-(trifluoromethyl)biphenyl-4-carbonitrile (500 mg, 1.91 mmol) and tetrahydrofuran (5 mL). To the mixture was added isobutylmagnesium bromide (2.87 mL, 5.74 mmol, 2M in THF). The reaction was heated at 100° C. in a microwave for 30 minutes. The reaction mixture was then carefully added to a solution of sodium borohydride (145 mg, 3.83 mmol) in methanol (5 mL). After stirring for 5 minutes, the mixture was concentrated to dryness. Purification by column chromatography gave 3-methyl-1-(2-methyl-4′-(trifluoromethyl)biphenyl-4-yl)butan-1-amine (470 mg). 1H NMR (400 MHz, CD3OD, δ): 7.72 (d, 2H), 7.50 (d, 2H), 7.24 (s, 1H), 7.19 (d, 2H), 3.94 (m, 1H), 2.27 (s, 3H), 1.65 (m, 2H), 1.49 (m, 1H), 0.95 (d, 3H), 0.92 (d, 3H).

Workup

  1. customA microwave reaction
  2. concentrationthe mixture was concentrated to dryness
  3. customPurification by column chromatography

Sources & evidence

ORD record
ord-4dfe9279142c4638a12cb8acd6d00807
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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