Potassium Phosphate, Tribasic → HCID 66696717, compound

HRID 1672564Notes

Reaction equation

HRID 1672564 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2[CH3:13])=[CH:4][C:3]=1[F:14].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH:23]1(B(O)O)[CH2:25][CH2:24]1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[CH:23]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:12][CH:11]=[N:10][C:9]=3[CH3:13])=[CH:4][C:3]=2[F:14])[CH2:25][CH2:24]1

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 66696592HCID 66696592, compound

Product 1

HCID 66696717HCID 66696717, compoundYield 185.5%

Reagents, catalysts & solvents 4

HCID 75806TricyclohexylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of Example 36A (870 mg, 3.40 mmol), Pd(OAc)2 (38.1 mg, 0.170 mmol), tricyclohexylphosphine (95 mg, 0.34 mmol), K3PO4 (2524 mg, 11.9 mmol), and cyclopropylboronic acid (379 mg, 4.42 mmol) in toluene (16 mL) and water (0.8 mL) was heated in a microwave reactor at 100° C. for 1.5 hr. A second, identical reaction was performed. The two reactions were combined, and then filtered, rinsed with EtOAc, and concentrated to an orange oil. The crude product was chromatographed on silica gel (Analogix® SF25-40G column, 0%-25% EtOAc/hexanes, 30 mL/min), which yielded 1.37 g (93%) of the title compound as yellow crystals. 1H NMR (300 MHz, CH3OH-d4) δ 8.13 (s, 1H), 7.35 (dd, J=8.1, 1.8 1H), 7.29 (dd, J=11.4, 1.8 1H), 7.06 (t, J=8.0, 1H), 2.39 (s, 3H), 2.17-2.05 (m, 1H), 1.03 (dd, J=8.5, 6.4, 4.3 2H), 0.81-0.73 (m, 2H). MS (DCI+) m/z 218 (M+H).

Workup

  1. customA second, identical reaction
  2. filtrationfiltered
  3. washrinsed with EtOAc
  4. concentrationconcentrated to an orange oil
  5. customThe crude product was chromatographed on silica gel (Analogix® SF25-40G column, 0%-25% EtOAc/hexanes, 30 mL/min), which

Sources & evidence

ORD record
ord-0c5b94991e564d0f8969be0ca9e8731b
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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