Phenylboronic Acid → HCID 23445658, compound

HRID 1280872Notes

Reaction equation

HRID 1280872 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].[CH2:21]([C:25]1[O:26][C:27]2[CH:50]=[CH:49][CH:48]=[CH:47][C:28]=2[C:29]=1[C:30](=[O:46])[C:31]1[CH:36]=[C:35](I)[C:34]([O:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44])=[C:33](I)[CH:32]=1)[CH2:22][CH2:23][CH3:24]>COCCOC.O.CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:21]([C:25]1[O:26][C:27]2[CH:50]=[CH:49][CH:48]=[CH:47][C:28]=2[C:29]=1[C:30]([C:31]1[CH:36]=[C:35]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:34]([O:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44])=[C:33]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:32]=1)=[O:46])[CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 17749109Barium hydroxide, octahydrateHCID 23445649HCID 23445649, compound

Product 1

HCID 23445658HCID 23445658, compoundYield 42.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

At ambient temperature, to a stirred mixture containing phenylboronic acid (0.454 g, 3.73 mmol), barium hydroxide octahydrate (1.60 g, 5.08 mmol) and palladium (II) acetate (7.60 mg, 0.0339 mmol) in DME:H2O (6:1, 20 mL) was added a solution of 2-n-butyl-3-(4-[(2-methoxyethoxy)methoxy]-3,5-diiodobenzoyl)benzofuran (1.07 g, 1.69 mmol) in DME:H2O (6:1, 20 mL). After the addition was complete, the reaction was heated at 80° C. for 16 h. The reaction was cooled to ambient temperature, diluted with ether (50 mL), washed sequentially with sat. aq. NaHCO3 (3×), with brine (3×), dried (MgSO4) and concentrated. The crude product was purified on Biotage KP-Sil eluting with 25% ether/pet. ether to give 0.380 g (42%) of the title compound. 1H NMR (DMSO-d6) δ 0.76 (t, 3H), 1.22 (sextet, 2H), 1.64 (quintet, 2H), 2.81-2.92 (m, 6H), 3.03 (s, 3H), 4.44 (s, 2H), 7.31-7.67 (m, 14H), 7.76 (s, 2H).

Workup

  1. additionAfter the addition
  2. temperatureThe reaction was cooled to ambient temperature
  3. washwashed sequentially with sat. aq. NaHCO3 (3×), with brine (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified on Biotage
  7. washKP-Sil eluting with 25% ether/pet. ether

Sources & evidence

ORD record
ord-32b7583ddd0348ee8012f5e934129c30
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

Loading…