Potassium Carbonate → HCID 57794652, compound

HRID 2099816Notes

Reaction equation

HRID 2099816 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH:7]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:8][C:9]2[CH:17]=[C:16]([CH3:18])[C:15]3[C:11](=[CH:12][N:13]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[N:14]=3)[CH:10]=2)[NH:5][CH:6]=1.[F:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH2:39]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH2:39][N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[C:4]1[CH:7]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])[CH2:8][C:9]1[CH:17]=[C:16]([CH3:18])[C:15]2[C:11](=[CH:12][N:13]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:25])[CH3:26])[N:14]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 178430869HCID 178430869, compound

Product 1

HCID 57794652HCID 57794652, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 1-(4-methyl-1H-imidazol-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethylcarbamate (38.4 mg, 0.079 mmol), 3-fluoro benzylbromide (10.8 μL, 0.083 mmol, 1.05 equiv), and potassium carbonate (22.0 mg, 0.16 mmol) were combined in dimethylformamide (1.0 mL). After stirring at room temperature for 16 h, the solvents were removed and the residue purified by column chromatography to afford 31.0 mg (64%). 1H-NMR (CD3OD, 300 MHz) δ −0.02 (s, 9H), 0.87-0.98 (m, 2H), 1.31 (s, 9H), 2.23 (s, 3H), 2.47 (s, 3H), 3.08-3.18 (m, 2H), 3.56-3.71 (m, 2H), 4.89-5.13 (m, 3H), 5.72 (s, 1H), 6.83-7.14 (m, 2H), 7.21 (s, 1H), 8.20 (s, 1H). Mass spec.: 594.47 (MH)+.

Workup

  1. customthe solvents were removed
  2. customthe residue purified by column chromatography
  3. customto afford 31.0 mg (64%)

Sources & evidence

ORD record
ord-0ac30115f9c440ed815024ebfb9fa5cb
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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