Potassium Carbonate → HCID 67453252, compound

HRID 1853919Notes

Reaction equation

HRID 1853919 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:5][C:4]=1[F:18].[NH:19]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:18][C:4]1[CH:5]=[C:6]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:7]=[CH:8][C:3]=1[CH2:2][N:19]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 982104-HydroxypyrrolidineHCID 467394222-[4-(Bromomethyl)-3-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 67453252HCID 67453252, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-[4-(bromomethyl)-3-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (300 mg, 0.95 mmol), pyrrolidin-3-ol (99 mg, 1.1 mmol), and potassium carbonate (160 mg, 1.1 mmol) in acetonitrile (5 mL) was heated to 50° C. for 3 h. The reaction mixture was cooled, filtered and the filtrate was concentrated to afford the desired product (280 mg, 92%) as a red oil: ESI MS m/z 322 [C17H25BFNO3+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9429bfefeab34ae69959bf7ce4ce6fec
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

Loading…