Dichloromethane → HCID 58899609, compound

HRID 2246635Notes

Reaction equation

HRID 2246635 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:24]([NH:26][C:27](=[O:44])[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=1)[CH3:25].C(=O)([O-])O.[Na+].C(Cl)Cl>C(O)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:24]([NH:26][C:27]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([N:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13][CH2:12]4)=[N:7][NH:8]3)=[CH:4][CH:3]=2)[CH:29]=1)=[O:44])[CH3:25]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 58899616HCID 58899616, compound2×HCID 60133236HCID 60133236, compound2×

Product 1

HCID 58899609HCID 58899609, compoundYield 82.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture, of 1,1-dimethylethyl 4-(6-bromo-1H-indazol-3-yl)-1-piperazinecarboxylate (Intermediate 6, 660 mg) N-ethyl-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 10, 598 mg) tetrakis(triphenylphosphine)palladium (25 mg) and aqueous sodium hydrogen carbonate (1M, 1.5 ml) in isopropanol (6 ml) was stirred at 150° C. for 20 min in a microwave oven. DCM and water were added and the organic phase was separated using a hydrophobic filter tube and concentrated under vacuum. The residue was purified by chromatography on a silica column eluting with a cyclohexane/ethyl acetate gradient to give the title compound (660 mg).

Workup

  1. customthe organic phase was separated
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by chromatography on a silica column
  4. washeluting with a cyclohexane/ethyl acetate gradient

Sources & evidence

ORD record
ord-c595b4cefe2e4419bf98c5a9c9295a3e
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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