Methyl iodide → HCID 68651293, compound

HRID 1949091Notes

Reaction equation

HRID 1949091 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9]([O:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])=[C:8]3[NH:21][C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][C:27]=4[C:7]3=[CH:6][C:5]2=1.[CH3:29][I:30]>ClCCl>[I-:30].[F:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:8]1[C:9]([O:15][CH2:16][CH2:17][N+:18]([CH3:29])([CH3:19])[CH3:20])=[C:10]3[NH:11][C:12]4[CH:13]=[CH:14][C:2]([F:1])=[CH:3][C:4]=4[C:5]3=[CH:6][C:7]2=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 45138929HCID 45138929, compound

Product 1

HCID 68651293HCID 68651293, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)-N,N-dimethylethanamine (14 mg) in dichloromethane (8 mL) was added MeI (1.0 mL) at RT under Ar. The resultant solution was stirred overnight and the solid formed. The solid was collected by filtration and washed once with dichloromethane and dried under vacuum to give the title compound (12 mg, 62%). 1H NMR (400 MHz, CD3OD) δ ppm 8.51 (s, 1H), 7.84 (dd, T=9.2, 2.8 Hz, 2H), 7.44 (dd, T=8.8, 4.0 Hz, 2H), 7.12 (ddd, J=9.2, 9.6, 2.4 Hz, 2H), 4.75-4.68 (m, 2H), 4.12-4.07 (m, 2H), 3.46 (s, 9H); MS (ESI) e/z 394 (M-I)+.

Workup

  1. customthe solid formed
  2. filtrationThe solid was collected by filtration
  3. washwashed once with dichloromethane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e4aa9d198dc646e89c5706e8239490ff
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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