Potassium Carbonate → HCID 86698706, compound

HRID 338365Notes

Reaction equation

HRID 338365 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][OH:10])=[C:4]([O:13][CH3:14])[CH:3]=1.[Cl:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][NH:22]2)=[CH:18][C:17]=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:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][NH:22]2)=[CH:18][C:17]=1[C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][OH:10])=[C:4]([O:13][CH3:14])[CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylateHCID 86698707HCID 86698707, compound

Product 1

HCID 86698706HCID 86698706, compoundYield 76.1%

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-methoxyphenoxy)propan-1-ol (97 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 purification by flash chromatography to give the title compound (92 mg, 76% yield) as a pale solid. 1H NMR (400 MHz, CD3OD) δ 8.01 (s, 1H), 8.00 (s, 1H), 7.58 (s, 1H), 7.03 (m, 2H), 7.00 (m, 1H), 4.18 (m, 2H), 3.87 (s, 3H), 3.80 (m, 2H), 3.37 (s, 3H), 2.05 (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. custompurification by flash chromatography

Sources & evidence

ORD record
ord-632e93250b5a45e497115814e6ce29c1
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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