Tetrahydrofuran → 2-(6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-pyridin-3-yl)-propan-2-ol

HRID 42208

Reaction equation

HRID 42208 reaction equation
C(OC(=O)[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)=[N:19][N:18]=3)[CH2:13][CH2:12]2)=[N:7][CH:6]=1)C.[CH3:36][Mg]I.[CH2:39]1[CH2:43][O:42]CC1>>[F:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]([N:14]3[CH2:13][CH2:12][N:11]([C:8]4[N:7]=[CH:6][C:5]([C:43]([OH:42])([CH3:39])[CH3:36])=[CH:10][CH:9]=4)[CH2:16][CH2:15]3)=[N:18][N:19]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 592406536-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinic acid ethyl esterHCID 178418373HCID 178418373, compound

Product 1

HCID 592405842-(6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-pyridin-3-yl)-propan-2-olYield 10%

Procedure

6-{4-[4-(4-Fluoro-benzyl)-phthalazin-1-yl]-piperazin-1-yl}-nicotinic acid ethyl ester (85 mg, 0.180 mmol) is dissolved in THF (1 mL). Methyl magnesium iodide (240 μL, 3M in diethyl ether, 0.72 mmol) is added dropwise. Stir reaction for 2 h at room temperature. Concentrate in vacuo. The residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2) to afford the title compound (8 mg, 10%).

Workup

  1. customreaction for 2 h at room temperature
  2. concentrationConcentrate in vacuo
  3. customThe residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ea976603e2204ac9bd075527618ef6cc
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Linked notes

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