Dimethylformamide → HCID 59161309, compound

HRID 545509Notes

Reaction equation

HRID 545509 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][CH:15]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([OH:25])[CH:11]=2.[CH2:29](I)[CH3:30].[H-].[Na+].CN(C)C=O>C(OCC)(=O)C>[CH2:29]([O:25][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]([CH2:5][C:4]1[CH:26]=[CH:27][CH:28]=[C:2]([F:1])[CH:3]=1)[C:18]1[CH2:17][CH2:16][CH:15]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[CH2:14][C:13]2=1)[CH3:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 59161260HCID 59161260, compound

Product 1

HCID 59161309HCID 59161309, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add N-[9-(3-fluoro-benzyl)-6-hydroxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (175 mg, 0.46 mmol), ethyl iodide (72 mg 0.46 mmol), and sodium hydride (60% suspension in mineral oil, 37 mg, 0.92 mmol) to dimethylformamide (1 mL) and stir at room temperature overnight. Dilute the reaction with ethyl acetate, wash with water (2×), dry over sodium sulfate, and concentrate. Recrystallize from ethyl acetate/hexanes to obtain the title compound (107 mg, 57%): MS (ES): m/z (M+1); 1H NMR (CDCl3): δ 7.28 (m, 1H), 7.11 (d, 1H), 6.98 (s, 1H), 6.97 (m, 1H), 6.82 (d, 1H), 6.79 (d, 1H), 6.65 (d, 1H), 5.58 (broad s, 1H, NH), 5.22 (s, 2H), 4.44 (m, 1H), 4.09 (q, 2H), 3.15 (dd, 1H), 2.60-2.81 (m, 3H), 2.33 (m, 1H), 2.15 (m, 2H), 1.45 (t, 1H), 1.18 (m, 6H).

Workup

  1. additionDilute
  2. washwash with water (2×)
  3. dry with materialdry over sodium sulfate
  4. concentrationconcentrate
  5. customRecrystallize from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a9097e9296d04b7ba962e500a973871b
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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