Toluene → HCID 86698617, compound

HRID 338270Notes

Reaction equation

HRID 338270 reaction equation
CC1(C)COB([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]3[CH2:18][O:17][CH2:16]3)=[CH:10][CH:9]=2)OC1.Br[C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][C:29]=1[Cl:30])[NH:26][CH:25]=[C:24]2[CH:31]=[O:32].C(=O)([O-])[O-].[K+].[K+].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].C(OCC)(=O)C>[Cl:30][C:29]1[CH:28]=[C:27]2[C:23]([C:24]([CH:31]=[O:32])=[CH:25][NH:26]2)=[CH:22][C:21]=1[C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:15]2[CH2:16][O:17][CH2:18]2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehydeHCID 86698616HCID 86698616, compound

Product 1

HCID 86698617HCID 86698617, compoundYield 87.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5,5-dimethyl-2-[4-(oxetan-3-yloxy)phenyl]-1,3,2-dioxaborinane (90 mg, 0.35 mmol) in ethanol (1.4 mL) was added 5-bromo-6-chloro-1H-indole-3-carbaldehyde (110 mg, 0.43 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (26 mg, 0.036 mmol), 2M aqueous potassium carbonate (0.7 mL, 1.4 mmol) and toluene (4 mL). The mixture was degassed with N2 for 3 min and heated to 110° C. by microwave irradiation for 1 h. The 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 Na2SO4 and concentrated in vacuo to give a residue, which was purified by flash chromatography on silica gel eluting with EtOAc/petroleum ether (1:10 to 1:1) to give 6-chloro-5-[4-(oxetan-3-yloxy)phenyl]-1H-indole-3-carbaldehyde (100 mg, 87%) as a colorless oil.

Workup

  1. customThe mixture was degassed with N2 for 3 min
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a residue, which
  4. washwashed with brine (2×10 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give a residue, which
  8. customwas purified by flash chromatography on silica gel eluting with EtOAc/petroleum ether (1:10 to 1:1)

Sources & evidence

ORD record
ord-3cf5f6cf0fc44bedb3bcc02196c58e7b
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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