Methanol → HCID 70896111, compound

HRID 2403676Notes

Reaction equation

HRID 2403676 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]([NH:13][CH3:14])=[O:12].CN1C[CH2:20][O:19][CH2:18]C1.C[OH:23]>>[CH3:14][NH:13][C:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:18]([O:19][CH3:20])=[O:23])[CH:3]=2)[NH:7][N:6]=1)=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 79724-MethylmorpholineHCID 70896114HCID 70896114, compound

Product 1

HCID 70896111HCID 70896111, compoundYield 61%

Conditions

Temperature
70 °C

Procedure

To a solution of 5-bromo-N-methyl-1H-indazole-3-carboxamide (710 mg, 2.8 mmol) in anhydrous methanol (20 mL) was added 1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride dichloromethane complex (400 mg, 0.56 mmol) and N-methylmorpholine (565 mg, 5.60 mmol). The reaction vessel was evacuated and back filled with nitrogen three times. The vessel was then filled with 30 psi carbon monoxide. The reaction mixture was heated to 70° C., increasing the pressure within the vessel to 45 psi. The reaction was agitated at 70° C. for 24 hours. The reaction mixture was cooled to room temperature and was filtered through Celite, rinsing with methanol. The filtrate was concentrated and purification by flash column chromatography gave the title compound (410 mg, 61%) as a brown solid. 1H NMR (400 MHz, DMSO-d6, δ): 13.9 (s, 1 H), 8.88 (s, 1 H), 8.49 (d, J=4.8, 1 H), 7.95-7.98 (m, 1 H), 7.68-7.70 (m, 1 H), 3.88 (s, 3 H), 2.82 (d, J=4.8 Hz, 3 H).

Workup

  1. customThe reaction vessel was evacuated
  2. additionback filled with nitrogen three times
  3. additionThe vessel was then filled with 30 psi carbon monoxide
  4. temperatureincreasing the pressure within the vessel to 45 psi
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationwas filtered through Celite
  7. washrinsing with methanol
  8. concentrationThe filtrate was concentrated
  9. custompurification by flash column chromatography

Sources & evidence

ORD record
ord-169702fc777b4b40b9a20fc808eeb0a8
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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