Aniline → HCID 57529294, compound

HRID 1454204Notes

Reaction equation

HRID 1454204 reaction equation
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[Br:43][C:44]1[CH:45]=[C:46]([CH:51]=[C:52](I)[CH:53]=1)[C:47]([O:49]C)=[O:48].[NH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[Br:43][C:44]1[CH:45]=[C:46]([CH:51]=[C:52]([NH:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:53]=1)[C:47]([OH:49])=[O:48]

Participants

8

Reactant 4

HCID 6115AnilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 21942573Methyl 3-bromo-5-iodobenzoateHCID 23676156Sodium t-butoxide

Product 1

HCID 57529294HCID 57529294, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of palladium(II) acetate (1.1 mg, 0.005 mmol) and xantphos (8.9 mg, 0.015 mmol) in toluene (8 ml) was stirred at room temperature for 5 min in a sealable tube purged with nitrogen, methyl 3-bromo-5-iodobenzoate (340 mg, 1.0 mmol) and aniline (111.8 mg, 1.2 mmol) were added and let stir for 5 more min, Sodium tert-butoxide (134.6 mg, 1.4 mmol) was then added and the mixture was stirred at room temperature for 5 min before heated up to 80° C. for 3 h. The reaction mixture was cooled down to RT and ether (containing 1% triethylamine) was added, passed through a celite column, dried over sodium sulfate and concentrated under vacuum to give the crude product which was used directly in the next reaction without further purification: HPLC retention time: 2.123 min (method A). MS (ESI) (M+H)+ 292.07.

Workup

  1. additionwere added
  2. additionwas then added
  3. temperaturebefore heated up to 80° C. for 3 h
  4. temperatureThe reaction mixture was cooled down to RT
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5a46003be5aa4f1ea7f3e0de892ae280
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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