Borane;tetrahydrofuran → HCID 68443036, compound

HRID 1435876Notes

Reaction equation

HRID 1435876 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[C:13]1[N:18]=[CH:17][C:16]([CH2:19][C:20]#[N:21])=[CH:15][CH:14]=1.B.C1COCC1>C1COCC1>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[C:13]1[N:18]=[CH:17][C:16]([CH2:19][CH2:20][NH2:21])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68442305HCID 68442305, compound

Product 1

HCID 68443036HCID 68443036, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [6-(6-methoxy[1,5]naphthyridin-4-yl)pyridin-3-yl]acetonitrile (0.26 g, 0.94 mmole), in THF (20 mL) at RT was added 1M BH3.THF (5 mL, 5.0 mmole). After 24 h, H2O (10 mL) wash added dropwise to the reaction solution followed by 1M HCl (10 mL). After 1 h, the reaction solution was made basic by addition of 6M NaOH (2 mL). The reaction contents were concentrated under vacuum and extracted with EtOAc (3×50 mL). The organic phase was dried over Na2SO4 and concentrated under vacuum affording the crude title compound as light orange solid which was used directly without further purification: LC-MS (ES) m/e 281 (M+H)+.

Workup

  1. washH2O (10 mL) wash
  2. additionadded dropwise to the reaction solution
  3. waitAfter 1 h
  4. additionthe reaction solution was made basic by addition of 6M NaOH (2 mL)
  5. customThe reaction contents
  6. concentrationwere concentrated under vacuum
  7. extractionextracted with EtOAc (3×50 mL)
  8. dry with materialThe organic phase was dried over Na2SO4
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1dddd87356b64738851fee480bb316a7
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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