Phenylboronic Acid → N-Boc-2-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

HRID 850029Notes

Reaction equation

HRID 850029 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15](Br)=[CH:16][C:10]=2[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[C:1]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][C:10]=2[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 19365864tert-Butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

Product 1

HCID 19365863N-Boc-2-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of N-Boc-2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (Step 1; 637 mg, 0.2 mmol), phenyl boronic acid (244 mg, 0.2 mmol), NaHCO3 (504 mg, 6 mmol) and tetrakis(triphenylphosphine)palladium(O) (116 mg, 0.1 mmol) in DME (10 mL) and water (10 mL) was heated to 80° C. for 20 h. The mixture was partitioned between water and EtOAc, washed with aqueous NaHCO3, water (2×) then brine, dried and evaporated. Column chromatography of the residue (silica gel; hexane/EtOAc 95:5) afforded the title compound as a viscous oil.

Workup

  1. customThe mixture was partitioned between water and EtOAc
  2. washwashed with aqueous NaHCO3, water (2×)
  3. dry with materialbrine, dried
  4. customevaporated

Sources & evidence

ORD record
ord-befedb2b7d194db6b8c81d6b9b809980
Source dataset
uspto-grants-2000_01
Patent number
US06015817

Reaction notes

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