Triethylamine → 6-Bromo-4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

HRID 60317Notes

Reaction equation

HRID 60317 reaction equation
[Br:1][C:2]1[N+:10]([O-])=[CH:9][C:8]2[N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]3[N:20]=[CH:21][CH:22]=[C:23]([Cl:24])[C:5]=3[C:4]=2[CH:3]=1.BrC1[N+]([O-])=CC2N(COCC[Si](C)(C)C)C3N=C(Cl)C=CC=3C=2C=1.C(N(CC)CC)C>C(#N)C>[Br:1][C:2]1[N:10]=[CH:9][C:8]2[N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19])[C:6]3[N:20]=[CH:21][CH:22]=[C:23]([Cl:24])[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 866560456-Bromo-4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-7-oxideHCID 866560466-bromo-2-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-7-oxide

Product 1

HCID 583650426-Bromo-4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-bromo-4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-7-oxide with 6-bromo-2-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-7-oxide (4:1, 90 mg, 0.2 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (8.5 mg, 0.012 mmol), and triethylamine (0.1 mL, 0.7 mmol) in acetonitrile (1.2 mL) was heated under microwave irradiation at 130° C. for 10 minutes. The cooled reaction mixture was concentrated in vacuo and purified by flash chromatography (silica, 40 g, ISCO, 0-40% ethyl acetate in heptane) to afford the title compound as a 4:1 mixture of the title compound with 6-bromo-2-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole as an off-white solid (60 mg, 70%). The mixture was used in subsequent steps without any further purification.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by flash chromatography (silica, 40 g, ISCO, 0-40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-39bba96841384a5f995f41a1a87ff984
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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