Potassium Carbonate → HCID 69071449, compound

HRID 2099832Notes

Reaction equation

HRID 2099832 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([CH2:15][C:16]1[CH:24]=[C:23]([CH3:25])[C:22]2[C:18](=[CH:19][N:20]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:21]=2)[CH:17]=1)[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[C:34]([C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CCCCCC>CN(C)C=O.C(OCC)(=O)C>[C:34]([C:38]1[CH:39]=[CH:40][C:41]([CH2:42][N:3]2[CH:4]=[CH:5][N:1]=[C:2]2[CH:6]([CH2:15][C:16]2[CH:24]=[C:23]([CH3:25])[C:22]3[C:18](=[CH:19][N:20]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:32])[CH3:33])[N:21]=3)[CH:17]=2)[CH2:7][C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])=[CH:44][CH:45]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 21226206Ethyl acetate hexaneHCID 69071554HCID 69071554, compound

Product 1

HCID 69071449HCID 69071449, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 3-(1H-imidazol-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate (0.16 mmol), 4-tert-butylbenzyl bromide (1.0 equiv), and potassium carbonate (1.0 equiv) in dimethylformamide (2 mL) was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (20 mL) and washed with water (3×5 mL). The ethyl acetate layer was dried, filtered and concentrated in vacuo. The product was obtained by flash chromatography using 0% to 50% ethyl acetate/hexane (65%). 1H-NMR (400 MHz, CDCl3) δ 7.93 (1H, s), 7.23 (2H, m), 7.03 (2H, m), 6.82 (2H, m), 6.63 (1H, s), 6.49 (1H,s), 5.68 (2H, s), 4.82 (2H, d, J=4.0 Hz), 3.60 (2H, t, 8.0 Hz), 3.41 (1H, m), 2.86 (2H, d, J=8.0 Hz), 2.79 (1H, dd, J1=8.0 Hz, J2=16 Hz), 2.61 (1H, dd, J1=8.0 Hz, J2=16 Hz), 2.49 (3H, s), 1.31 (9H, s), 1.25 (9H, s), 0.91 (2H, t, J=8.0 Hz), −0.06 (9H,s). MS(ESI)[M+H]+=617.

Workup

  1. washwashed with water (3×5 mL)
  2. dry with materialThe ethyl acetate layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was obtained by flash chromatography

Sources & evidence

ORD record
ord-8090caba39034001b4840009a1db42c9
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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