Dimethylformamide → HCID 59457850, compound

HRID 1711778Notes

Reaction equation

HRID 1711778 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[C:14]([C:17]4[N:24]5[C:20]([O:21][CH:22]=[CH:23]5)=[N:19][C:18]=4[C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[CH:15]=[CH:16][C:11]3=[N:10][N:9]=2)=[C:4]([F:32])[CH:3]=1.[NH2:33][CH2:34][C:35]([CH3:39])([CH3:38])[CH2:36][OH:37].CN([CH:43]=[O:44])C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:32][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[C:8]1[N:12]2[CH:13]=[C:14]([C:17]3[N:24]4[C:20]([O:21][CH:22]=[CH:23]4)=[N:19][C:18]=3[C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:15]=[CH:16][C:11]2=[N:10][N:9]=1)[C:43]([NH:33][CH2:34][C:35]([CH3:39])([CH3:38])[CH2:36][OH:37])=[O:44]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 59457821HCID 59457821, compound

Product 1

HCID 59457850HCID 59457850, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(4-bromo-2-fluorophenyl)-6-[6-(4-fluorophenyl)-imidazo[2,1-b]oxazol-5-yl]-[1,2,4]triazolo[4,3-a]pyridine (0.20 g, 0.41 mmol; Example #K.1.3), 3-amino-2,2-dimethyl-propan-1-ol (0.21 g, 2.0 mmol; Lancaster), and TEA (0.175 mL, 1.21 mmol) in DMF (5 mL) was vacuum purged with carbon monoxide three times followed by the addition of dichlorobis(triphenylphosphine)palladium (II) (0.03 g, 0.04 mmol) and subsequent vacuum purging with carbon monoxide five times. The reaction was heated at about 100° C. under an atmosphere of carbon monoxide for about 2 h after which the reaction was cooled and concentrated under reduced pressure. The crude material was dissolved in DCM and purified by flash chromatography using DCM/MeOH (90:10) as eluent. After concentration of the clean fractions, the resulting oil was triturated with Et2O. The resulting solid was filtered and dried to provide the title compound as a light yellow solid (0.19 g, 85%): LC/MS (Table 1, Method a) Rt=2.11 min; MS m/z: 543.2 (M+H)+.

Workup

  1. custompurged with carbon monoxide three times
  2. custompurging with carbon monoxide five times
  3. temperaturewas cooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe crude material was dissolved in DCM
  6. custompurified by flash chromatography
  7. customAfter concentration of the clean fractions, the resulting oil was triturated with Et2O
  8. filtrationThe resulting solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-a20b4c9cf39541a192b70d5a6f833a4f
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

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