Sodium hydride → HCID 68709159, compound

HRID 2239352Notes

Reaction equation

HRID 2239352 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3]1.[H-].[Na+].F[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16]>CN(C=O)C>[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 678803-FluorobenzonitrileHCID 295970(1-methylpyrrolidin-3-yl)methanol

Product 1

HCID 68709159HCID 68709159, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(1-Methylpyrrolidin-3-yl)methanol (0.500 g, 4.34 mmol) was dissolved in dry DMF (8 mL), cooled (<0° C.), NaH (0.260 g, 6.51 mmol, 55% in oil) added and stirred for 30 minutes. 3-Fluorobenzonitrile (0.552 g, 4.56 mmol) was added and the reaction mixture allowed to warm to r.t. over 1 h. Due to excessive foaming the reaction mixture was diluted with dry DMF to 20 mL and stirred over night at r.t. The reaction was quenched by addition of water portionwise, and the mixture was extracted with DCM. The organic phase was dried over a phase separator and concentrated in vacuo. The product was purified by flash chromatography using a step gradient of EtOAc:MeOH:TEA (100:10:2) in EtOAc to give the title compound as an oil. Yield: 0.573 g (58%). 1H NMR (400 MHz, CDCl3) δ 7.30-7.35 (m, 1H), 7.18-7.22 (m, 1H), 7.09-7.12 (m, 1H), 7.07-7.09 (m, 1H), 3.86 (d, 2H, J=6.95 Hz), 2.54-2.67 (m, 3H), 2.40-2.51 (m, 2H), 2.33 (s, 3H), 2.00-2.10 (m, 1H), 1.51-1.61 (m, 1H).

Workup

  1. additionadded
  2. stirringstirred over night at r.t
  3. customThe reaction was quenched by addition of water portionwise
  4. extractionthe mixture was extracted with DCM
  5. customThe organic phase was dried over a phase separator
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-6d76f7a96b774a13b9bd02b72313927b
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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