Water → HCID 59662591, compound

HRID 1015066Notes

Reaction equation

HRID 1015066 reaction equation
Br[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.B(O)O.C1C[O:18][CH2:17][CH2:16]1.[C:20]([O-])([O-])=O.[K+].[K+].[OH2:26]>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>[CH3:20][CH:2]1[C:11]2[C:6](=[C:7]3[C:8](=[CH:9][CH:10]=2)[O:18][CH2:17][CH2:16][O:26]3)[CH2:5][CH2:4][NH:3]1

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 61668Boronic AcidHCID 54291263HCID 54291263, compound

Product 1

HCID 59662591HCID 59662591, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

1 mmol of either isomer of bromo-1,2,3,4-tetrahydro-isoquinoline, 2 eq. of corresponding boronic acid, and 12,5 mol % of Pd(PPh3)4 are placed in a microwave reactor vial (Personal Chemistry). 3 ml of THF and 2 eq of K2CO3 in 1 ml H2O are added via syringe and the vial is purged with argon. The vial is heated by microwaves at 120° C. for 40 minutes. After cooling the mixture is partitioned between CH2Cl2 and water (30 mL each). The organic layer is washed with water, brine, dried over anhydrous Na2SO4, filtered and evaporated at reduced pressure. The residue is dissolved in diethyl ether (2 mL) and treated with excess of ethereal solution of hydrogen chloride. The precipitate is collected by filtration, washed and dried to give sufficiently pure title compound as a hydrochloride salt.

Workup

  1. customthe vial is purged with argon
  2. temperatureAfter cooling the mixture
  3. customis partitioned between CH2Cl2 and water (30 mL each)
  4. washThe organic layer is washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated at reduced pressure
  8. dissolutionThe residue is dissolved in diethyl ether (2 mL)
  9. additiontreated with excess of ethereal solution of hydrogen chloride
  10. filtrationThe precipitate is collected by filtration
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-deefc5eb207b47f2af0a797651ddfb10
Source dataset
uspto-grants-2011_07
Patent number
US07985753B2

Reaction notes

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