Sodium hydride → HCID 67343910, compound

HRID 1850085Notes

Reaction equation

HRID 1850085 reaction equation
[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([OH:23])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[H-].[Na+]>CN(C=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([O:23][C:4]2[CH:3]=[C:2]([Br:1])[C:9]([CH3:10])=[CH:8][C:5]=2[C:6]#[N:7])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 341754194-Bromo-2-fluoro-5-methylbenzonitrile

Product 1

HCID 67343910HCID 67343910, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to Example 28 using 4-bromo-2-fluoro-5-methyl-benzonitrile (1.0 g, 4.7 mmol), 3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (1.1 g, 6.5 mmol), DMF (20 mL) and NaH (60% in mineral oil, 156 mg, 6.5 mmol) to provide the title compound (1.3 g, 74%). MS (ESI): mass calcd. for C16H19BrN2O3, 366.1. m/z found, 389.1 [M+Na]+. 1H NMR (CDCl3): 7.45 (s, 1H), 6.83 (s, 1H), 4.97-4.88 (m, 1H), 4.35 (ddd, J=9.8, 6.4, 0.9 Hz, 1H), 4.09 (dd, J=10.0, 3.9 Hz, 1H), 2.36 (s, 3H), 1.47 (s, 9H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1ed62ddc8b374dd8aecc9f47fb54f19d
Source dataset
uspto-grants-2015_02
Patent number
US08957059B2

Reaction notes

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