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Potassium Phosphate, Tribasic → HCID 18186387, compound

HRID 1358041
Notes
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Reaction equation

HRID 1358041 reaction equation
Br[C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[N:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1>COCCOC>[F:31][C:28]1[CH:27]=[CH:26][C:25]([N:8]2[CH2:9][CH2:10][C:11]3[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:12]=3)[CH:7]2[CH2:6][C:5]2[CH:4]=[CH:3][C:2]([C:45]3[CH:46]=[CH:47][N:42]=[CH:43][CH:44]=3)=[CH:33][CH:32]=2)=[CH:30][CH:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734379(Pyridin-4-yl)boronic acidHCID 181864091-(4-Bromobenzyl)-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 18186387HCID 18186387, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 80711,2-Dimethoxyethane
Solvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4-bromobenzyl)-6-phenylmethoxy-2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline (500 mg, 1 mmol) in ethylene glycol dimethyl ether (15 mL) was added potassium phosphate (2.12 g, 10 mmol) and pyridine-4-boronic acid (185 mg, 1.5 mmol). The reaction mixture was heated to 90° C. for 18 hours under nitrogen. The resulting mixture was concentrated and water added and extracted with ethyl acetate. The organic layer was dried using sodium sulfate, filtered and concentrated to give a crude black oil. The oil was purified by column chromatography (SiO2, 40% ethyl acetate/hexanes) to provide the title compound (260 mg, 50% yield): ES-MS (m/z) 501 [M+H]+, 1H NMR (CDCl3) δ 8.64 (d, 2H), 7.49 (m, 4H), 7.38 (m, 5H), 7.13 (d, 2H), 6.92 (t, 2H), 6.78 (m, 3H), 6.72 (s, 2H), 5.04 (s, 2H), 4.79 (t, 1H), 3.59 (m, 1H), 3.49 (m, 2H), 3.22 (m, 1H), 3.01 (m, 1H), 2.71 (t, 1H).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additionwater added
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude black oil
  8. customThe oil was purified by column chromatography (SiO2, 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9abc349d1ad34463adf0d183680b3c68
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06593322B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes