Phenylboronic Acid → HCID 59730978, compound

HRID 416135Notes

Reaction equation

HRID 416135 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:11][C:12]2[C:21]3[CH2:20][CH:19]([OH:22])[CH2:18][CH2:17][C:16]=3[CH:15]=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)C>[C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([NH:11][C:12]2[C:21]3[CH2:20][CH:19]([OH:22])[CH2:18][CH2:17][C:16]=3[CH:15]=[CH:14][CH:13]=2)=[O:10])[CH:3]=1

Participants

9

Reactant 4

HCID 66827Phenylboronic AcidHCID 80271Tri-o-tolylphosphineHCID 17749109Barium hydroxide, octahydrateHCID 59730973HCID 59730973, compound

Product 1

HCID 59730978HCID 59730978, compoundYield 26.2%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

Next, to a mixture of 2-(3-bromophenyl)-N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)acetamide (50.0 mg, 0.139 mmol), phenyl boronic acid (25.4 mg, 0.208 mmol), tri-o-tolylphosphine (8.45 mg, 0.028 mmol), and barium hydroxide octahydrate (65.7 mg, 0.208 mmol) in 12 mL of ethylene glycol dimethyl ether was added ethanol (4 mL), water (4 mL), and palladium(II) acetate (3.12 mg, 0.014 mmol). The mixture was stirred vigorously under argon and was heated to reflux. After cooled to room temperature, water was added and the product was extracted with ethylacetate. The organic layer was washed with water then brine, dried over MgSO4, filtered, and concentrated under reduced pressure to obtain 2-biphenyl-3-yl-N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)acetamide (13.0 mg, 26% yield).

Workup

  1. temperaturewas heated to reflux
  2. extractionthe product was extracted with ethylacetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4064b7deb50f4bb4979eac62ae7964f2
Source dataset
uspto-grants-2012_01
Patent number
US08088826B2

Reaction notes

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