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Potassium Carbonate → 3-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]propanoic acid

HRID 338441
Notes
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Reaction equation

HRID 338441 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1B1OCC(C)(C)CO1.[C:19](=O)([O-])[O-:20].[K+].[K+].Br[C:26]1[CH:37]=[CH:36][C:29]([O:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:28][CH:27]=1>O1CCOCC1.CN(C=O)C.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:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:19]=[O:20])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:26]1[CH:37]=[CH:36][C:29]([O:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:28][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 74720343-(4-Bromophenoxy)propanoic acidHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

Product 1

HCID 866987723-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]propanoic acidYield 87%

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 6228DimethylformamideSolvent
HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (150 mg, 0.57 mmol) in dioxane (5 mL) and DMF (1 mL) was added N,N-dimethylformiminium chloride (155 mg, 1.21 mmol). The reaction mixture was stirred at room temperature for 20 min. 2N potassium carbonate (314 mg, 2.28 mmol), 3-(4-bromophenoxy)propanoic acid (139 mg, 0.57 mmol) and Pd(dppf)Cl2 (21 mg, 0.028 mmol) were then added. The reaction was degassed with N2 and heated to 90° C. for 30 min. The reaction was extracted with ethyl acetate (10 mL×2). The organic layers were washed with brine (10 mL), dried over sodium sulfate, and concentrated to give the title compound (170 mg, 87% yield) as a brown oil.

Workup

  1. customThe reaction was degassed with N2
  2. temperatureheated to 90° C. for 30 min
  3. extractionThe reaction was extracted with ethyl acetate (10 mL×2)
  4. washThe organic layers were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d8d1fe2962e04dd1a8a5cf0acaf355f5
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889730B2

Reaction notes

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