Sodium Fluoride → C-(5-benzyloxy-thiophen-2-yl)methylamine

HRID 2080245Notes

Reaction equation

HRID 2080245 reaction equation
[CH2:1]([O:8][C:9]1[S:13][C:12]([C:14]#[N:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[F-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[S:13][C:12]([CH2:14][NH2:15])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5235Sodium FluorideHCID 21226445Aluminium lithium hydrideHCID 23130497HCID 23130497, compound

Product 1

HCID 23130661C-(5-benzyloxy-thiophen-2-yl)methylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-benzyloxy-thiophene-2-carbonitrile described in Preparation Example 81 (30 mg, 0.14 mmol) in tetrahydrofuran (3 mL) was added lithium aluminum hydride (21 mg, 0.557 mmol), which was then stirred for 1.5 hours at room temperature. Sodium fluoride (240 mg, 5.72 mmol) was added to the reaction mixture, which was stirred for 2 hours, then, on an ice bath, 10% hydrous tetrahydrofuran (2 mL) was added. The reaction mixture was filtered through Celite pad, the filtrate was concentrated and C-(5-benzyloxy-thiophen-2-yl)methylamine (32 mg, 0.147 mmol) was obtained as a crude product. The title compound (3 mg, 0.008 mmol, 5.4%) was obtained from this and quinoline-6-carboxylic acid (26 mg, 0.15 mmol) according to an analogous method to Example H-1.

Workup

  1. stirringwas stirred for 2 hours
  2. filtrationThe reaction mixture was filtered through Celite pad
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-41f9ce1f07274a41be847a11bfa43fec
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…