Sodium Carbonate → HCID 67958183, compound

HRID 1529292Notes

Reaction equation

HRID 1529292 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[F:9].[NH:10]1[C:18]2[C:13](=[CH:14][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.C(Cl)Cl>[F:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][CH:11]=[CH:12]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1235571-Bromo-2,6-difluorobenzeneHCID 27347725-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Product 1

HCID 67958183HCID 67958183, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 22272177Toluene waterSolvent

Conditions

Temperature
125 °C

Procedure

A glass microwave reaction vessel was charged with 1-bromo-2,6-difluorobenzene (1.145 mL, 7.71 mmol) and 5-indoleboronic acid pinacol ester (1.50 g, 6.17 mmol) in toluene/H2O (4:1, 15 mL) followed by dichloro(1,1-bis(diphenylphosphinoferrocene)) palladium(ii) complex with DCM (0.252 g, 0.309 mmol) and Na2CO3 (0.645 mL, 15.43 mmol). The reaction mixture was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 125° C. for 4 h, and then the mixture was diluted with DCM. The organic layer was separated, washed with water, dried over Na2SO4, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 10-15% EtOAc in Hexanes) to give 5-(2,6-difluorophenyl)-1H-indole (1.06 g, 4.62 mmol, 74.9% yield) as a light yellow oil. MS (ESI, pos. ion) m/z: 230 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel chromatography (eluting with 10-15% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-2ce294ecc7d948ce80b59d39e9590742
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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