Phenylboronic Acid → HCID 59730978, compound

HRID 130646Notes

Reaction equation

HRID 130646 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-7ce1317420e94333a07f800d83d3dd10
Source dataset
uspto-grants-2008_06
Patent number
US07381840B2

Reaction notes

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