Potassium Carbonate → HCID 86698704, compound

HRID 338363Notes

Reaction equation

HRID 338363 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][OH:10])=[C:4]([F:13])[CH:3]=1.[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][NH:21]2)=[CH:17][C:16]=1B1OCC(C)(C)CO1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CCO.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][NH:21]2)=[CH:17][C:16]=1[C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][OH:10])=[C:4]([F:13])[CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 43393691HCID 43393691, compoundHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate

Product 1

HCID 86698704HCID 86698704, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 3-(4-bromo-2-fluorophenoxy)propan-1-ol (93 mg, 0.37 mmol), methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (100 mg, 0.31 mmol) and potassium carbonate (128 mg, 0.93 mmol) in Toluene/EtOH (5 mL, 3:1) and water (1 ml) was added Pd(dppf)Cl2 (22 mg, 0.031 mmol). The mixture was degassed and purged with nitrogen for 5 minutes, then allowed to heat to 110° C. and stirred for 30 minutes. The reaction mixture was concentrated in vacuo to give a brown residue. The residue was purified by flash chromatography to give the title compound (85 mg, 73% yield) as a pale solid. 1H NMR (400 MHz, CD3OD) δ 8.04 (d, 2H), 7.61 (m, 2H), 7.18 (m, 2H), 4.21 (m, 2H), 3.89 (s, 3H), 3.82 (t, 2H), 2.08 (m, 2H).

Workup

  1. customThe mixture was degassed
  2. custompurged with nitrogen for 5 minutes
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give a brown residue
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3326534c6032400cad2ded4125741ac8
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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