Sodium hydride → HCID 86653005, compound

HRID 242102Notes

Reaction equation

HRID 242102 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([C:10]2([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([OH:24])[CH:22]=4)[CH2:17][CH2:16][N:15]=3)[CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=1.[C:25]([O:29][C:30](=[O:35])[NH:31][CH2:32][CH2:33]Br)([CH3:28])([CH3:27])[CH3:26]>CCCCC.CN(C)C=O.O>[Cl:3][C:4]1[N:9]=[C:8]([C:10]2([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:33][CH2:32][NH:31][C:30](=[O:35])[O:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=4)[CH2:17][CH2:16][N:15]=3)[CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 58246369HCID 58246369, compound

Product 1

HCID 86653005HCID 86653005, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 8003PentaneSolvent

Conditions

Temperature
40 °C

Procedure

90% suspension of sodium hydride in oil (37 mg, 1.387 mmol) was washed with n-pentane and suspended in dry dimethylformamide (5 ml). (1-[1-(6-Chloropyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol (217 mg, 0.69 mmol) dissolved in dimethylformamide (1 ml) was added dropwise. After stirring at room temperature for 1 hour a solution of tert-butyl-2-bromoethylcarbamate (466 mg, 2.08 mmol) in dimethylformamide (2 ml) was added dropwise. The reaction mixture was heated to 40° C. for 4 hours. The reaction mixture was diluted with water (30 ml) and extracted with dichloromethane (3×). The combined organic extracts were washed with brine twice, dried (MgSO4) and concentrated in vacuo. The crude product was used for the next step without further purification.

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. extractionextracted with dichloromethane (3×)
  4. washThe combined organic extracts were washed with brine twice
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-eca4ed1a53d24cf7827ebf267f8eab90
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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