Sodium hydride → HCID 86653005, compound

HRID 1850882Notes

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>[C:25]([O:29][C:30](=[O:35])[NH:31][CH2:32][CH2:33][O:24][C:21]1[CH:22]=[C:23]2[C:18]([CH2:17][CH2:16][N:15]=[C:14]2[C:10]2([C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([Cl:3])[N:9]=3)[CH2:13][CH2:12][CH2:11]2)=[CH:19][CH:20]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

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

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

Sources & evidence

ORD record: ord-9cec4fcf210844ac9bc4035f3187a762
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957089B2

Reaction notes

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