Sodium Carbonate → benzyl 2-(5-(4'-amino-[1,1'-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetate

HRID 515390Notes

Reaction equation

HRID 515390 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][O:12][CH:11]([CH2:14][C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]3[CH2:13][O:12][CH:11]([CH2:14][C:15]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[O:16])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346154-Aminophenylboronic acidHCID 89872727benzyl 2-(5-(4-bromophenyl)tetrahydro-2H-pyran-2-yl)acetate

Product 1

HCID 89872737benzyl 2-(5-(4'-amino-[1,1'-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetateYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of benzyl 2-(5-(4-bromophenyl)tetrahydro-2H-pyran-2-yl)acetate (300 mg, 0.771 mmol) in dioxane (6 ml) at room temperature was added 4-aminophenylboronic acid (211 mg, 1.541 mmol), Pd(Ph3P)4 (178 mg, 0.154 mmol) and 2M Na2CO3 (1.541 ml, 3.08 mmol) and the mixture was degassed and heated at 120° C. in microwave for 30 min. The reaction was quenched by sat. aq. NH4Cl and was extracted with EtOAc. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (10 to 50% EtOAc (2% TEA)/Heptane) to give the title compound 250 mg (yield 81%). MS (ESI) m/z 402.3 (M+1). Retention time 1.48 min (condition A).

Workup

  1. customthe mixture was degassed
  2. customThe reaction was quenched by sat. aq. NH4Cl
  3. extractionwas extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (10 to 50% EtOAc (2% TEA)/Heptane)

Sources & evidence

ORD record
ord-6dd5f49507834eb5a1d7cddff8114853
Source dataset
uspto-grants-2015_08
Patent number
US09108956B2

Reaction notes

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