Sodium hydride → HCID 59818263, compound

HRID 402523Notes

Reaction equation

HRID 402523 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)CCO1.[H-].[Na+].[CH2:14]([O:21][C:22]1[C:31]2[C:26](=[CH:27][C:28](F)=[C:29]([Cl:32])[CH:30]=2)[CH:25]=[CH:24][N:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:34][C:35](N(C)C)=[O:36]>>[CH2:14]([O:21][C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:11][CH:8]3[CH2:7][CH2:6][C:5]4([O:1][CH2:34][CH2:35][O:36]4)[CH2:10][CH2:9]3)=[C:29]([Cl:32])[CH:30]=2)[CH:25]=[CH:24][N:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 31374Dimethylacetamide2×HCID 598182521-Benzyloxy-7-chloro-6-fluoro-isoquinolineHCID 86623504HCID 86623504, compound

Product 1

HCID 59818263HCID 59818263, compound

Procedure

1.26 g (8.34 mmol) of dioxa-spiro[4.5]decan-8-ol were dissolved in 50 ml of dimethyl acetamide and 695.2 mg (17.4 mmol) of sodium hydride (60%) were added. After stirring for 30 minutes at room temperature a solution of 2.0 g (6.95 mmol) of 1-benzyloxy-7-chloro-6-fluoro-isoquinoline (11) in 50 ml of dimethyl acetamide was added and stirring was continued at room temperature. After 1 h the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried with magnesium sulfate and evaporated, which gave 3.30 g of the crude product, which was used without further purification. Rt=2.05 min (Method C). Detected mass: 426.5 (M+H+).

Workup

  1. additionwas added
  2. customwas continued at room temperature
  3. customAfter 1 h the solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-7ab359a7fa37474181c14e7573f67415
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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