Dichloromethane → HCID 86698709, compound

HRID 338367Notes

Reaction equation

HRID 338367 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1B1OCC(C)(C)CO1.Br[C:24]1[CH:29]=[CH:28][C:27]([C:30]2([OH:34])[CH2:33][O:32][CH2:31]2)=[C:26]([O:35][CH3:36])[CH:25]=1.C(=O)([O-])[O-].[K+].[K+].ClCCl>C1(C)C=CC=CC=1.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].O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]2([OH:34])[CH2:33][O:32][CH2:31]2)=[C:26]([O:35][CH3:36])[CH:25]=1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylateHCID 86698710HCID 86698710, compound

Product 1

HCID 86698709HCID 86698709, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (70 mg, 0.27 mmol) and 3-(4-bromo-2-methoxyphenyl)oxetan-3-ol (96 mg, 0.30 mmol) in toluene (1.2 mL), ethanol (0.6 mL), and tetrahydrofuran (0.6 mL) followed by the addition of 2M potassium carbonate aqueous (0.6 mL, 1 mmol). Nitrogen was bubbled through the reaction for 5 minutes then [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium, dichloromethane (25 mg, 0.031 mmol) was added and the reaction heated to 115° C. for 16 hours. The reaction was then cooled to room temperature and filtered through a pad of celite washing with ethyl acetate. The filtrate was concentrated under reduced pressure and passed through silica yielding 104 mg of the title compound that was brought forward without further purification. MS (ES+) 386.1 (M−H)+.

Workup

  1. customNitrogen was bubbled through the reaction for 5 minutes
  2. temperatureThe reaction was then cooled to room temperature
  3. filtrationfiltered through a pad of celite
  4. washwashing with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customwas brought forward without further purification

Sources & evidence

ORD record
ord-7f3249fdd2f8457fa902b73c228715e6
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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