Sodium hydride → 4-[[4-fluoro-3-[4-(3-methylpyridin-2-yl)oxypiperidine-1-carbonyl]phenyl]methyl]-2H-phthalazin-1-one

HRID 1091753Notes

Reaction equation

HRID 1091753 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)=[CH:4][C:3]=1[C:20]([N:22]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]1)=[O:21].[H-].[Na+].F[C:32]1[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][N:33]=1>CN(C)C(=O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)=[CH:4][C:3]=1[C:20]([N:22]1[CH2:23][CH2:24][CH:25]([O:28][C:32]2[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][N:33]=2)[CH2:26][CH2:27]1)=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2427222-Fluoro-3-methylpyridineHCID 441993164-(4-fluoro-3-(4-hydroxypiperidine-1-carbonyl)benzyl)phthalazin-1(2H)-one

Product 1

HCID 577918164-[[4-fluoro-3-[4-(3-methylpyridin-2-yl)oxypiperidine-1-carbonyl]phenyl]methyl]-2H-phthalazin-1-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of crude 4-[[4-fluoro-3-(4-hydroxypiperidine-1-carbonyl)phenyl]methyl]-2H-phthalazin-1-one (2a) (50 mg, 0.131 mmol) in N,N-dimethylacetamide (1 mL) was treated with sodium hydride (60% in mineral oil; 3.8 mg, 0.157 mmol) and the reaction was left stirring at ambient temperature until effervescence had stopped. 2-fluoro-3-methylpyridine (16 mg, 0.144 mmol) was then added and the reaction mixture sealed into a microwave tube, heated to 170° C. and held at that temperature for 250 seconds before cooling to ambient temperature. The mixture was then purified by preparative HPLC to afford the desired material; m/z (LC-MS, ESI+), RT=4.22 (M+H 473.2)

Workup

  1. waitthe reaction was left
  2. customthe reaction mixture sealed into a microwave tube
  3. temperatureheated to 170° C.
  4. temperaturebefore cooling to ambient temperature
  5. customThe mixture was then purified by preparative HPLC

Sources & evidence

ORD record
ord-708e77a8e02f45a3a6e3f06438dc8fb6
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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