Triphenylphosphine → HCID 25017619, compound

HRID 1664955Notes

Reaction equation

HRID 1664955 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH:19]([NH:22][C:23]([C:25]4[CH:30]=[CH:29][C:28](Br)=[CH:27][N:26]=4)=[O:24])[CH2:18][CH2:17]3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:34]1(B(O)O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(=O)([O-])[O-].[Na+].[Na+].COCCOC>[F:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH:19]([NH:22][C:23]([C:25]4[CH:30]=[CH:29][C:28]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[CH:27][N:26]=4)=[O:24])[CH2:18][CH2:17]3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 66627769HCID 66627769, compound

Product 1

HCID 25017619HCID 25017619, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
85 °C

Procedure

5-Bromo-pyridine-2-carboxylic acid (4-{2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl}-cyclohexyl)-amide (example 30A66, step 1) (80 mg, 0.155 mmol) and phenylboronic acid (27 mg, 0.22 mmol) were dissolved under argon in 0.4 ml 2M sodium carbonate and 1.6 ml 1,2-dimethoxyethane. Triphenylphosphine (16 mg, 0.062 mmol) and Pd(II)acetate (7 mg, 0.03 mmol) were added and the mixture stirred at 85° C. for 16 hrs. The reaction mixture was extracted with water and two times dichloromethane. The organic extracts were washed with water and brine, dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient). The desired compound was obtained as a brown solid (36 mg, 45%), MS: m/e=514.1 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with water and two times dichloromethane
  2. washThe organic extracts were washed with water and brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient)

Sources & evidence

ORD record
ord-5a31d66d62914298acdc3907ec93d266
Source dataset
uspto-grants-2011_10
Patent number
US08039490B2

Reaction notes

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