Dichloromethane → HCID 178458279, compound

HRID 1433189Notes

Reaction equation

HRID 1433189 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6]B(O)[C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]1=2.Br[C:14]1[CH:34]=[CH:33][C:17]2[NH:18][C:19]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[N:20][C:16]=2[CH:15]=1.C(Cl)Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.COCCOC.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:32][C:29]([F:30])([F:31])[C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][C:19]2[NH:18][C:17]3[CH:33]=[CH:34][C:14]([C:4]4[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=4[C:2]([OH:6])([CH3:12])[CH3:1])=[CH:15][C:16]=3[N:20]=2)=[CH:24][CH:25]=1

Participants

8

Reactant 3

HCID 6344DichloromethaneHCID 442289743,3-Dimethyl-1,3-dihydro-2,1-benzoxaborol-1-olHCID 178506219HCID 178506219, compound

Product 1

HCID 178458279HCID 178458279, compoundYield 30.7%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3,3-dimethyl-3H-benzo[c][1,2]oxaborol-1-ol (66.5 mg, 0.411 mmol), 5-bromo-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzimidazole (76.2 mg, 0.205 mmol), PdCl2(dppf)2.CH2Cl2 (34 mg, 0.041 mmol), and tetrabutylammonium bromide (66 mg 0.205 mmol) in 8 mL of DME and 1.64 mL of Na2CO3 solution (1.0 M) was degassed and purged with argon twice. The mixture was then heated to 90° C. for 12 h. The mixture was then cooled to room temperature, and filtered though a pad of Celite 545. The filtrate was concentrated under reduced pressure to yield a dark brown oil. The residue was purified by chromatography (silica, ethyl acetate:hexanes, 1:1) to afford the title compound as an off-white solid (26.8 mg, 30%). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.81 (dd, 1H, J=8.1 Hz, J=1.1 Hz), 7.63 (m, 2H), 7.56 (m, 1H), 7.45 (m, 1H), 7.34 (td, 1H, J=7.8 Hz, J=1.5 Hz), 7.16-7.26 (m, 4H), 7.05 (dd, 1H, J=7.4 Hz, J=1.7 Hz), 5.44 (s, 2H), 1.32 (s, 6H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C24H21F3N2O2: 427.43 (M+H), Found 427.1.

Workup

  1. custompurged with argon twice
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationfiltered though a pad of Celite 545
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto yield a dark brown oil
  6. customThe residue was purified by chromatography (silica, ethyl acetate:hexanes, 1:1)

Sources & evidence

ORD record
ord-cf4239b813a24b7aaaec7c876a4830aa
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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