Reaction equation
[F:1][CH:2]([F:20])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9](CCCN(C)C)[N:8]=[C:7]2I.[CH:21]([Mg]Cl)(C)C.[CH2:26]([Sn:30]([CH2:35][CH2:36][CH2:37][CH3:38])(Cl)[CH2:31][CH2:32][CH3:33])[CH2:27][CH2:28][CH3:29]>C1COCC1>[F:20][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[Sn:30]([CH2:35][CH2:36][CH2:37][CH3:38])([CH2:31][CH2:32][CH2:33][CH3:21])[CH2:26][CH2:27][CH2:28][CH3:29]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(5-(difluoromethoxy)-3-iodo-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine (1.2 g, 2.78 mmol) in dry THF (25 mL) was added isopropylmagnesium chloride (1.5 mL, 2M in THF, 3 mmol) drop-wise at −16° C. under nitrogen atmosphere. The reaction was stirred for 30 minutes, then dibutylchloro (propyl)stannane (3.3 mL, 3.6 mmol) was added dropwise at −16° C. under nitrogen, then the reaction mixture was slowly warmed to room temperature and stirred for 2 hours. The reaction mixture was quenched with a solution of saturated NH4Cl (40 mL) and product extracted with EtOAc (3×30 mL), organics combined dried with sodium sulfate, filtered and concentrated. Crude oil used into the next step without further purification (1.1 g, crude).
Workup
- stirringstirred for 2 hours
- customThe reaction mixture was quenched with a solution of saturated NH4Cl (40 mL) and product
- extractionextracted with EtOAc (3×30 mL)
- dry with materialorganics combined dried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customCrude oil used into the next step without further purification (1.1 g, crude)
Sources & evidence
- ORD record
- ord-564934e42e8c41d48052eebbcfd37fb0
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Linked notes
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