Tributylamine → HCID 86592988, compound

HRID 1348943Notes

Reaction equation

HRID 1348943 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:40]([O:44][CH2:45][CH3:46])(=[O:43])[CH:41]=[CH2:42].C(N(CCCC)CCCC)CCC>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:45]([O:44][C:40](=[O:43])[CH:41]=[CH:42][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9]2)=[CH:4][CH:3]=1)[CH3:46]

Participants

7

Reactant 4

HCID 7622TributylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 109688311-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Product 1

HCID 86592988HCID 86592988, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-bromo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (2.6 g, Reference Example 7), tri-o-tolylphosphine (0.37 g), palladium (II) acetate, ethyl acrylate (1.6 mL) and tributylamine (8.01 mL) in dry dimethylformamide (25 mL), under argon, was heated at 155° C. for 3 hours then stood at room temperature overnight. The reaction mixture was evaporated and the resulting black oil was partitioned between ethyl acetate (200 mL) and hydrochloric acid (200 mL, 2M). The organic phase was washed with hydrochloric acid (200 mL, 2M), then with water (100 mL), then with brine (100 mL), then dried over magnesium sulfate and then evaporated. The residual yellow oil was subjected to flash chromatography on silica under gradient elution conditions with a mixture of ethyl acetate and pentane (from 3:97 to 10:90, v/v) to give the title compound. LC-MS: RT=4.05 minutes; no molecular ion observed.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe resulting black oil was partitioned between ethyl acetate (200 mL) and hydrochloric acid (200 mL, 2M)
  3. washThe organic phase was washed with hydrochloric acid (200 mL, 2M)
  4. dry with materialwith water (100 mL), then with brine (100 mL), then dried over magnesium sulfate
  5. customevaporated
  6. washThe residual yellow oil was subjected to flash chromatography on silica under gradient elution conditions with a mixture of ethyl acetate and pentane (from 3:97 to 10:90

Sources & evidence

ORD record
ord-d566f0bf5ad944289c0d5cafa4bfc648
Source dataset
uspto-grants-2007_05
Patent number
US07211586B2

Reaction notes

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