Tributylamine → HCID 69859806, compound

HRID 1883715Notes

Reaction equation

HRID 1883715 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:11](Br)=[C:10]2[C:6]=1[CH2:7][CH2:8][CH2:9]2)(=[O:3])[CH3:2].[C:15]([O:20][CH2:21][CH3:22])(=[O:19])/[CH:16]=[CH:17]/[CH3:18].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CCCC)CCCC)CCC>CN(C)C=O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:11]([C:17]([CH3:18])=[CH:16][C:15]([O:20][CH2:21][CH3:22])=[O:19])=[C:10]2[C:6]=1[CH2:7][CH2:8][CH2:9]2)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 7622TributylamineHCID 80271Tri-o-tolylphosphineHCID 429065Ethyl trans-crotonateHCID 12683815HCID 12683815, compound

Product 1

HCID 69859806HCID 69859806, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-acetylamino-7-bromoindane (2.8 g, prepared according to the method of A. Courtin, Helv. Chim. Acta 1980, 63(8), pages 2280-2286), ethyl crotonate (2.51 g), palladium diacetate (150 mg), tri-ortho-tolyl phosphine (450 mg) and tributylamine (10 mL) in dimethylformamide (30 mL) was stirred at 120° C. for 4 hours under a nitrogen atmosphere. The mixture was cooled to room temperature, then allowed to stand for 48 hours, then partitioned between ethyl acetate (500 mL) and aqueous hydrochloric acid (300 mL, 1M). The organic phase was washed with 5% aqueous sodium bicarbonate (150 mL) and then filtered. The clear yellow filtrate was dried over sodium sulfate then evaporated. The residue was subjected to normal phase HPLC on silica under gradient elution conditions using ethyl acetate, heptane and methanol mixtures (from 20:80:1 to 90/10/1, v/v/v) to give the title compound (1.9 g).

Workup

  1. customprepared
  2. custompartitioned between ethyl acetate (500 mL) and aqueous hydrochloric acid (300 mL, 1M)
  3. washThe organic phase was washed with 5% aqueous sodium bicarbonate (150 mL)
  4. filtrationfiltered
  5. dry with materialThe clear yellow filtrate was dried over sodium sulfate
  6. customthen evaporated
  7. washThe residue was subjected to normal phase HPLC on silica under gradient elution conditions

Sources & evidence

ORD record
ord-c251122a0417482ea9848f96c421eeba
Source dataset
uspto-grants-2004_07
Patent number
US06762199B2

Reaction notes

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