1,2-Dimethoxyethane → HCID 25121515, compound

HRID 2400585Notes

Reaction equation

HRID 2400585 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]4[CH:25]=[CH:24]C(C)=[CH:22][CH:21]=4)[N:14]=3)[O:11][CH:12]=2)=[CH:4][CH:3]=1.[C:27]1(B2OC(C)(C)C(C)(C)O2)[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].CO[CH2:50][CH2:51]OC>C1(P([Pd-4](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)C=CC=CC=1>[C:27]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:9]=[C:10]([C:13]4[CH:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]5[CH:21]=[CH:22][C:50]([CH3:51])=[CH:24][CH:25]=5)[N:14]=4)[O:11][CH:12]=3)=[CH:6][CH:7]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 109326752-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 25121166HCID 25121166, compound

Product 1

HCID 25121515HCID 25121515, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 178420553HCID 178420553, compoundCatalyst

Procedure

A mixture of 4-(4-bromophenyl)-2-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,3-oxazole (Example 75, 200 mg, 0.49 mmol), 2-cyclohex-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (158 μl, 0.74 mmol), sodium carbonate (0.49 ml, 2M aqueous solution, 0.98 mmol) and tetrakis(triphenylphosphino)palladium(0) (57 mg, 0.05 mmol) in 1,2-dimethoxyethane (3 ml) was heated to reflux for 18 h. After cooling to rt, the mixture was filtered over a pad of celite. The filtrate was diluted with ethyl acetate and successively washed with 0.1 N aqueous HCl and water. The organic layer was dried (MgSO4), filtered and concentrated to dryness. The crude material was purified by preparative HPLC to afford the title compound as a white solid (115 mg, 57%): 1H NMR (400 MHz, DMSO-d6) 8.60 (s, 1H), 7.78 (d, 2H), 7.49 (d, 2H), 7.17 (d, 2H), 7.08 (d, 2H), 6.67 (s, 1H), 6.23 (m, 1H), 5.37 (s, 2H), 2.41-2.37 (m, 2H), 2.28 (s, 3H), 2.27 (s, 3H), 2.22-2.17 (m, 2H), 1.77-1.70 (m, 2H), 1.64-1.59 (m, 2H); ES-MS m/z 410, HPLC RT (Method D) 3.48 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. filtrationthe mixture was filtered over a pad of celite
  4. additionThe filtrate was diluted with ethyl acetate
  5. washsuccessively washed with 0.1 N aqueous HCl and water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-d595cdf6b4b6434886f0c352c2cabecd
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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