Dimethylformamide → 1-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one

HRID 876210Notes

Reaction equation

HRID 876210 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=NN[CH:13]=2)[O:3]1.I[CH2:16][CH:17]1[CH2:22]C[O:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+].[CH3:29][N:30](C=O)C>>[CH3:29][N:30]1[C:22]2[C:17](=[CH:16][CH:13]=[C:9]([B:4]3[O:3][C:2]([CH3:14])([CH3:1])[C:6]([CH3:8])([CH3:7])[O:5]3)[CH:10]=2)[CH2:18][C:19]1=[O:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 27955074-(Iodomethyl)oxane

Product 1

HCID 717432781-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-oneYield 3.8%

Conditions

Temperature
80 °C

Procedure

2 g (10.3 mmol) 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2.9 mL (20.6 mmol) 4-(iodomethyl)-tetrahydro-2H-pyran are dissolved in 200 mL DMF and 4.274 g (30.9 mmol) K2CO3 are added. The mixture is shaken at 80° C. for 5 h. After cooling to r.t. the mixture is filtered, the filtrate is concentrated in vacuo to approximately 60 mL. The product is separated using HPLC-MS (Gilson, mass flow 120 mL/min, 10 μm, 200 g Sunfire RP18, ACN/water/TFA). The product fractions are combined and freeze-dried to yield 115 mg product (3.8%) R7.6.

Workup

  1. temperatureAfter cooling to r.t. the mixture
  2. filtrationis filtered
  3. concentrationthe filtrate is concentrated in vacuo to approximately 60 mL
  4. customThe product is separated
  5. customfreeze-dried

Sources & evidence

ORD record
ord-cfbf0f90f3024513baa3f41cad8b9393
Source dataset
uspto-grants-2015_03
Patent number
US08987249B2

Reaction notes

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