2,6-Di-tert-butyl-4-methylphenol → HCID 15232193, compound

HRID 2380401Notes

Reaction equation

HRID 2380401 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=3[C:18]=2[N:19]=1)(=O)=O.[C:22]1([Sn](C)(C)C)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[Li+].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOCC>[C:22]1([C:7]2[CH:8]=[CH:9][C:10]3[NH:11][C:12]4[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=4[C:18]=3[N:19]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 123095Stannane, trimethylphenyl-HCID 433294Lithium ChlorideHCID 152321942-trifluoromethanesulfonyloxy-6,7,8,9-tetrahydro-5H-pyrido[3,2-b]indole

Product 1

HCID 15232193HCID 15232193, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-trifluoromethanesulfonyloxy-6,7,8,9-tetrahydro-5H-pyrido[3,2-b]indole (99 mg, 0.31 mmol), phenyltrimethyltin (300 mg, 1.24 mmol), lithium chloride (40 mg, 0.93 mmol), tetrakis(triphenylphosphine)palladium(0) (7 mg, 0.02 mol. eq.) and a crystal of 2,6-di-tert-butyl-4-methylphenol in 1,4-dioxane (2 mL) were refluxed for 10 hours under an atmosphere of nitrogen. The mixture was cooled and poured into ether and filtered through celite. The ether was extracted with 15% hydrochloric acid. The pH of the acidic, aqueous phase was raised to about pH 10 with 28% ammonium hydroxide, then was extracted with ether. The extract was washed with water and brine, dried over sodium sulfate, filtered and concentrated. Purification by silica-gel chromatography (30% ethyl acetate in hexanes) gave 2-phenyl-6,7,8,9-tetrahydro-5H-pyrido[3,2-b]indole (Compound 4) as a white solid, m.p. 164°-165° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. extractionThe ether was extracted with 15% hydrochloric acid
  4. temperatureThe pH of the acidic, aqueous phase was raised to about pH 10 with 28% ammonium hydroxide
  5. extractionwas extracted with ether
  6. washThe extract was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica-gel chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7518abed04f3441a84aa9a8d040c9123
Source dataset
uspto-grants-1994_11
Patent number
US05367077

Reaction notes

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