Ethanol → HCID 87168273, compound

HRID 538029Notes

Reaction equation

HRID 538029 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[NH:7]1[C:15]2[C:10](=[CH:11][C:12](B(O)O)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.CCO.[Cl:22][C:23]1[N:24]=[N:25][C:26](Cl)=[CH:27][CH:28]=1>O.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.C1(C)C=CC=CC=1>[Cl:22][C:23]1[N:24]=[N:25][C:26]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][CH:8]=[CH:9]3)=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 27343615-Indolylboronic acid

Product 1

HCID 87168273HCID 87168273, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of Na2CO3 (0.70 g, 6.6 mmol) in H2O (5 mL) was added indole-5-boronic acid (1.0 g, 6.2 mmol) and EtOH (25 mL). After stirring at rt for 30 min, 3,6-dichloropyridazine (935 mg, 6.30 mmol), toluene (50 mL) and Pd(PPh3)4 (0.30 g) were added. The mixture was stirred at 90° C. for 30 h and then evaporated in vacuo. The residue was treated with CH2Cl2 (100 mL), washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography, eluting with (CH2Cl2-MeOH=100:5) to give 0.35 g (37% yield) of the product as a yellow solid. 1H NMR (DMSO-d6) δ 6.52 (1H, s), 7.40 (1H, s), 7.50 (1H, d, 6.3 Hz), 7.86-7.90 (2H, m), 8.27 (1H, d, 6.9 Hz), 8.32 (1H, s), 11.32 (1H, s). MS m/e 230 (M+H+); Calculated MW: 229 for C12H8ClN5.

Workup

  1. stirringThe mixture was stirred at 90° C. for 30 h
  2. customevaporated in vacuo
  3. additionThe residue was treated with CH2Cl2 (100 mL)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with (CH2Cl2-MeOH=100:5)

Sources & evidence

ORD record
ord-11941c0ed47f458e81dc2e3ba80535b1
Source dataset
uspto-grants-2014_10
Patent number
US08865719B2

Reaction notes

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