Dimethylformamide → HCID 57537482, compound

HRID 1693718Notes

Reaction equation

HRID 1693718 reaction equation
[Br:1][C:2]1[C:3](Cl)=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2=[N:6][CH:7]=1.CO[CH:30]([OH:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[H-].[Na+].CN(C)[CH:42]=[O:43]>>[Br:1][C:2]1[C:3]([O:37][CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:43][CH3:42])=[CH:35][CH:36]=2)=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 13736807HCID 13736807, compoundHCID 57537472HCID 57537472, compound

Product 1

HCID 57537482HCID 57537482, compoundYield 74%

Procedure

5-Bromo-4-chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (245 mg, 0.52 mmol) and methoxybenzyl alcohol (723 mg, 5.2 mmol) were dissolved in dimethylformamide (0.25 mL). Sodium hydride (167 mg, 4.2 mmol) was added and the mixture was irradiated in a Personal Chemistry Optimizer at 120° C. for 5 min. The reaction was quenched with water, applied to a Varian chemelut cartridge and eluted with ethyl acetate. The crude product was purified by flash silica gel chromatography using a gradient of (ethyl acetate and methanol 9:1) in hexanes to afford 5-Bromo-4-(4-methoxy-benzyloxy)-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (220 mg, 0.38 mmol, 74% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.39 (s, 1H), 7.66 (s, 1H), 7.40 (m, 1H), 7.35 (dd, J=7 Hz, J2=2 Hz, 1H), 7.08 (d, J=8 Hz, 1H), 7.01 (td, J1=7 Hz, J2=1 Hz, 1H), 6.77 (m, 4H), 5.63 (s, 2H), 4.37 (s, 2H), 3.71 (s, 3H), 3.64 (s, 3H), 3.58 (t, J=8 Hz, 1H), 0.83 (t, J=8 Hz, 1H), −0.08 (s, 9H). MS: m/z 569.4/571.3 (M+H+).

Workup

  1. customthe mixture was irradiated in a Personal Chemistry Optimizer at 120° C. for 5 min
  2. customThe reaction was quenched with water
  3. washeluted with ethyl acetate
  4. customThe crude product was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-e6781c9859f24c0bb0b1f6ea6df4bb4a
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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