Triethylamine → HCID 66765016, compound

HRID 1466763Notes

Reaction equation

HRID 1466763 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH3:19])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CN([CH:30]=[O:31])C.[CH3:32][OH:33]>N#N.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:32][O:33][C:30](=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH3:19])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21901440N,N-dimethylformamide methanolHCID 667653273-(3-Bromo-phenylsulfanyl)-6-chloro-2-methyl-1H-indole

Product 1

HCID 66765016HCID 66765016, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 947NitrogenSolvent

Conditions

Temperature
80 °C

Procedure

3-(3-Bromo-phenylsulfanyl)-6-chloro-2-methyl-1H-indole (4.764 g, 13.5 mmol) was combined with triethylamine (4.7 mL, 33.75 mmol) in DMF:MeOH (1:1, 150 mL) and N2 (g) was bubbled through the mixture for 30 minutes. (1,1′-Bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.988 g, 1.35 mmol) was added to the reaction then CO (g) at atmospheric pressure was bubbled in for 30 seconds. The reaction was then heated under an atmosphere of CO at 80° C. for 4 hours followed by standard workup. The crude material was purified by silica gel chromatography (0-30% EtOAc in hexanes) to afford the title compound.

Workup

  1. customwas bubbled through the mixture for 30 minutes
  2. customCO (g) at atmospheric pressure was bubbled in for 30 seconds
  3. customThe crude material was purified by silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d99c0cf0fc104fb3b7117d89016d158a
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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