Dimethyl(methylene)ammounium iodide → N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-methanamine

HRID 1678257Notes

Reaction equation

HRID 1678257 reaction equation
[CH3:1][N+:2]([CH3:4])=[CH2:3].[I-].[CH3:6][C:7]1([CH3:23])[C:11]([CH3:13])([CH3:12])[O:10][B:9]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[CH:17]3)[O:8]1>CC#N.CC(O)=O>[CH3:3][N:2]([CH3:4])[CH2:1][C:17]1[C:16]2[C:20](=[CH:21][CH:22]=[C:14]([B:9]3[O:10][C:11]([CH3:13])([CH3:12])[C:7]([CH3:23])([CH3:6])[O:8]3)[CH:15]=2)[NH:19][CH:18]=1

Participants

5

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 27347725-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Product 1

HCID 59024064N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-methanamineYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of Eschenmoser's salt (0.91 g, 4.9 mmol) in CH3CN (3 mL) and HOAc (1.5 mL) at rt was added a solution of 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (1.0 g, 4.1 mmol) in CH3CN (3 mL) dropwise over about 10 min. After about 2 hours, the reaction was quenched with saturated aqueous NaHCO3 and extracted with CH2Cl2 (3×15 mL). The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated to give crude N,N-Dimethyl-1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl]methanamine (0.60 g, 50%); RP-HPLC (Table 1, Method g) Rt 1.39 min; 1H NMR (d6-DMSO, 400 MHz) δ11.26 (br s, 1H), 8.07 (s, 1H), 7.44 (d, J=8.2 Hz, 1H), 7.37 (m, 2H), 3.92 (s, 2H), 2.40 (s, 6H), 1.31 (s, 12H).

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with CH2Cl2 (3×15 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-561b93aae0fc44f29fc11e56b7d50149
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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