Water → HCID 89885978, compound

HRID 2174070Notes

Reaction equation

HRID 2174070 reaction equation
Br[C:2]1[C:10]2[C:9]([CH:11]=[O:12])=[C:8]([CH3:13])[CH:7]=[C:6]([CH3:14])[C:5]=2[N:4]([S:15]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:3]=1.[CH3:25][Si:26]([CH3:46])([CH3:45])[CH2:27][CH2:28][O:29][CH2:30][N:31]1[C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][CH:33]=[N:32]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.C(Cl)Cl.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>[CH3:13][C:8]1[CH:7]=[C:6]([CH3:14])[C:5]2[N:4]([S:15]([C:18]3[CH:19]=[CH:20][C:21]([CH3:22])=[CH:23][CH:24]=3)(=[O:17])=[O:16])[CH:3]=[C:2]([C:35]3[N:31]([CH2:30][O:29][CH2:28][CH2:27][Si:26]([CH3:46])([CH3:45])[CH3:25])[N:32]=[CH:33][CH:34]=3)[C:10]=2[C:9]=1[CH:11]=[O:12]

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 447552015-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazoleHCID 86701699HCID 86701699, compound

Product 1

HCID 89885978HCID 89885978, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 3-bromo-5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde (100 mg, 0.246 mmol), 1-(2-trimethylsilylethoxy)methyl-1H-pyrazole-5-boronic acid pinacol ester (CAS #: 903550-12-9) (239 mg, 0.738 mmol), and K3PO4 (157 mg, 0.738 mmol) in DME (1 mL)/H2O (0.5 mL) was added Pd(PPh3)4 (56.9 mg, 0.049 mmol), and then the mixture was stirred at 80° C. for 16 h. The reaction mixture was cooled down to room temperature. The mixture was diluted with CH2Cl2. The bi-phase layer was partitioned. The organic layer was separated, dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel flash column chromatography [heptane/(30% EtOAc in CH2Cl2)=1/0 to 4/6] to give the title compound. MS (ESI+) m/z 524.2 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. customThe bi-phase layer was partitioned
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel flash column chromatography [heptane/(30% EtOAc in CH2Cl2)=1/0 to 4/6]

Sources & evidence

ORD record
ord-8a1fc11931864dcfbc150b599200a9d1
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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