Acetonitrile → HCID 86620730, compound

HRID 913774Notes

Reaction equation

HRID 913774 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=2.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:28][C:29]([NH2:31])=[O:30].CC#N>CCOC(C)=O>[C:17]([C:9]1[C:10]([C:13]([F:16])([F:15])[F:14])=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([CH2:28][C:29]([NH2:31])=[O:30])[C:4]([CH2:3][C:2]([F:1])([F:19])[F:20])=[CH:12]2)#[N:18]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 86620728HCID 86620728, compound

Product 1

HCID 86620730HCID 86620730, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 374A) (0.050 g, 0.17 mmol), Cs2CO3 (0.112 g, 0.34 mmol), 2-bromoacetamide (0.047 g, 0.34 mmol) and CH3CN (4 mL) was stirred at 70° C. for 2 h. The mixture was diluted with EtOAc (25 mL), washed with water (15 mL), brine (1 5 mL), dried over (MgSO4) and concentrated. The residue was stirred in EtOAc (5 mL) for 30 min. The resulting solid was filtered, rinsed with hexanes and dried to afford the title compound (0.017 g, 28%) as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ 7.88 (d, J=8.6 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.72 (s, 1H), 7.38 (s, 1H), 6.78 (s, 1H), 5.01 (s, 2H), 4.07 (q, 2H); MS m/z 348 (M−H).

Workup

  1. washwashed with water (15 mL), brine (1 5 mL)
  2. dry with materialdried over (MgSO4)
  3. concentrationconcentrated
  4. stirringThe residue was stirred in EtOAc (5 mL) for 30 min
  5. filtrationThe resulting solid was filtered
  6. washrinsed with hexanes
  7. customdried

Sources & evidence

ORD record
ord-32b31761bf6d45acadb0877dbb959ac7
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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