Ethanol → HCID 86698628, compound

HRID 338282Notes

Reaction equation

HRID 338282 reaction equation
CC1(C)COB([C:8]2[CH:20]=[CH:19][C:11]([O:12][CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])=[CH:10][CH:9]=2)OC1.Br[C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][C:31]=1[Cl:32])[NH:28][CH:27]=[C:26]2[CH:33]=[O:34].C(=O)([O-])[O-].[K+].[K+].C(O)C>C1(C)C=CC=CC=1.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].C(OCC)(=O)C>[Cl:32][C:31]1[CH:30]=[C:29]2[C:25]([C:26]([CH:33]=[O:34])=[CH:27][NH:28]2)=[CH:24][C:23]=1[C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]([CH3:17])([CH3:18])[CH2:15][OH:16])=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehydeHCID 86698627HCID 86698627, compound

Product 1

HCID 86698628HCID 86698628, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenoxy]-2,2-dimethylpropan-1-ol (60 mg, 0.21 mmol) in toluene (6 mL) was added 5-bromo-6-chloro-1H-indole-3-carbaldehyde (64 mg, 0.25 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (15 mg, 0.021 mmol), 2M aqueous potassium carbonate (0.42 mL, 0.84 mmol) and ethanol (2 mL). The reaction mixture was degassed with nitrogen for 3 min and heated to 110° C. by microwave irradiation for 1 h. The cooled reaction mixture was concentrated in vacuo to give a residue, which was dissolved with ethyl acetate (30 mL) and washed with brine (2×10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to give a residue, which was purified by flash chromatography to give 6-chloro-5-[4-(3-hydroxy-2,2-dimethylpropoxy)phenyl]-1H-indole-3-carbaldehyde (60 mg, 82%) as an off-white solid.

Workup

  1. customThe reaction mixture was degassed with nitrogen for 3 min
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customto give a residue, which
  5. washwashed with brine (2×10 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give a residue, which
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-bbc03aa28d034fb5bb0e83fc8c9956ed
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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