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Sodium Carbonate → HCID 59595873, compound

HRID 2075146
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Reaction equation

HRID 2075146 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14](B(O)O)=[CH:13][C:12]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH2:27][N:26](C(=O)C(F)(F)F)[CH2:25][CH2:24]2.BrC1C=CC=C2C=1CN(C(=O)C(F)(F)F)CC2.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.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.C1(C)C=CC=CC=1>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[CH2:27][NH:26][CH2:25][CH2:24]4)=[CH:13][C:12]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 231554111-(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanoneHCID 594631661-(8-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanoneHCID 59595866(5-Benzylbenzofuran-2-yl)boronic acid

Product 1

HCID 59595873HCID 59595873, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 5-benzylbenzofuran-2-ylboronic acid (252 mg, 1.0 mmole) in ethanol (3 mL) was added to a mixture of 1-(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone and 1-(8-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone (308 mg, 1.0 mmole), Pd(PPh3)4, toluene, and 2 M Na2CO3(3.5 mL). The resulting mixture was heated at reflux overnight. The reaction was concentrated in vacuo, and the residue was diluted with water. The aqueous phase was extracted with EtOAc (3×50 mL). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on ISCO column (5% to 10% MeOH/CH2Cl2) to provide the title compounds (189 mg, 56%). 1H NMR (400 MHz, CDCl3) δ 7.60 (m, 2H), 7.39 (dd, 1H), 7.37 (s, 1H), 7.25 (m, 5H), 7.10 (dd, 2H), 6.90 (s, 1H), 4.10 (s, 2H), 3.40 (s, 2H), 3.18 (m, 2H), 2.94 (m, 2H). MS (ESI) m/z: Calculated: 339.16; Observed: 340.10 (M++1).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction was concentrated in vacuo
  4. additionthe residue was diluted with water
  5. extractionThe aqueous phase was extracted with EtOAc (3×50 mL)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified on ISCO column (5% to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4819b9989f6d4f1f93c186a0ff393ce6
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07919519B2

Reaction notes

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