Acetonitrile → HCID 86620730, compound

HRID 2102208Notes

Reaction equation

HRID 2102208 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-ea3777504bac4d329c06d61a3f95a7c8
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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