Potassium Phosphate, Tribasic → HCID 178495764, compound

HRID 1470013Notes

Reaction equation

HRID 1470013 reaction equation
Br[C:2]1[S:6]/[C:5](=[N:7]\[C:8]([C:10]23[CH2:17][CH:16]4[CH2:18][CH:12]([CH2:13][CH:14]2[CH2:15]4)[CH2:11]3)=[O:9])/[N:4]([CH2:19][CH2:20][O:21][CH3:22])[CH:3]=1.[CH:23]1(B(O)O)[CH2:25][CH2:24]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:23]1([C:2]2[S:6]/[C:5](=[N:7]\[C:8]([C:10]34[CH2:17][CH:16]5[CH2:18][CH:12]([CH2:13][CH:14]3[CH2:15]5)[CH2:11]4)=[O:9])/[N:4]([CH2:19][CH2:20][O:21][CH3:22])[CH:3]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 178495762HCID 178495762, compound

Product 1

HCID 178495764HCID 178495764, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22272177Toluene waterSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with the product from Example 130B (150.0 mg, 0.39 mmol), cyclopropylboronic acid (Aldrich) (86 mg, 0.51 mmol), K3PO4 (212 mg, 1.36 mmol) and dichlorobis(trichlorohexylphosphine)palladium (II) (29 mg, 0.04 mmol) in 5 mL of H2O/toluene (1:1). The mixture was warmed to 100° C. and stirred overnight. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water. The organic extract was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on SiO2 using a gradient of 0% to 100% ethyl acetate:hexane to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 0.59-0.65 (m, 2H), 0.86-0.95 (m, 2H), 1.53-1.61 (m, 4H), 1.65-1.79 (m, 4H), 1.86-1.97 (m, 1H), 2.04-2.13 (m, 2H), 2.22-2.29 (m, 2H), 2.51-2.56 (m, 1H), 3.24 (s, 3H), 3.66 (t, J=5.3 Hz, 2H), 4.20 (t, J=5.4 Hz, 2H), 7.15 (d, J=1.0 Hz, 1H); MS (ESI+) m/z 347 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on SiO2 using a gradient of 0% to 100% ethyl acetate

Sources & evidence

ORD record
ord-13bfc1f6566049a39356e600ab0ca691
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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