Dimethylformamide → HCID 178518303, compound

HRID 2236667Notes

Reaction equation

HRID 2236667 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)C=NC/[C:5]/2=[CH:12]\[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[C:17]([OH:25])[CH:16]=1.[O:26]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27]1.C([O-])([O-])=[O:35].[Na+].[Na+].C[N:41]([CH3:44])[CH:42]=[O:43]>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>[F:23][CH:22]([F:24])[O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][NH:13]/[CH:12]=[C:5]2\[C:44](=[O:35])[NH:41][C:42](=[O:43])[C:3]3[C:4]\2=[CH:9][C:10]([C:28]2[CH:29]=[CH:30][O:26][CH:27]=2)=[CH:11][CH:2]=3)=[CH:16][C:17]=1[OH:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 86619583HCID 86619583, compound

Product 1

HCID 178518303HCID 178518303, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of example 180 (155.4 mg, 0.354 mmol), 3-furanboronic acid (47.51 mg, 0.425 mmol), tetrakis(triphenylphosphine)palladium(0) (40.46 mg, 0.035 mmol) and Na2CO3 (75.05 mg, 0.708 mmol) in 3 mL 80% N,N-dimethylformamide (DMF)/H2O is reacted in microwave at 150° C. for 6 minutes. The reaction mixture is partitioned in ethyl acetate/water. The aqueous layer is separated and extracted 2 times with ethyl acetate. The combined organic extracts were evaporated in vacuo. The resulting residue is treated with 1 mL MeOH/CH2Cl2 and the fine solid precipitated out of solution. It is allowed to sit at room temperature overnight. The precipitate is filtered to get 73.4 mg (48.6%) product as a yellow solid: MS (ESI) m/z 425.2 (M−H)−1; HRMS: calcd for C22H16F2N2O5+H+, 427.11001. found (EFI FT, [M+H]1+), 427.11023; 1H NMR (400 MHz, DMSO-D6) ppm 4.66 (d, J=6.30 Hz, 2 H) 6.70-6.90 (m, 1 H) 6.91-7.03 (m, 1 H) 7.06-7.23 (m, 2 H) 7.45 (dd, J=8.18, 1.38 Hz, 1 H) 7.82 (t, J=1.76 Hz, 1 H) 7.88-8.09 (m, 2 H) 8.36 (s, 1 H) 8.75 (d, J=13.09 Hz, 1 H) 10.02 (s, 1 H) 10.47-10.75 (m, 1H) 10.98 (s, 1 H); Analysis for C22H16F2N2O5: Calcd: C, 61.97; H, 3.78; N, 6.57. Found: C, 62.22; H, 3.74; N, 6.94.

Workup

  1. customThe reaction mixture is partitioned in ethyl acetate/water
  2. customThe aqueous layer is separated
  3. extractionextracted 2 times with ethyl acetate
  4. customThe combined organic extracts were evaporated in vacuo
  5. additionThe resulting residue is treated with 1 mL MeOH/CH2Cl2
  6. customthe fine solid precipitated out of solution
  7. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-65ae1be1aa2342e6ab61b829a2faf3d0
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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