Water → 6-Bromo-2-(diethoxymethyl)-1H-pyrrolo[3,2-c]pyridine

HRID 2205933Notes

Reaction equation

HRID 2205933 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[N:10](S(C)(=O)=O)[C:4]=2[CH:3]=1.[OH-].[Na+].O>CO>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH:15]([O:16][CH2:17][CH3:18])[O:19][CH2:20][CH3:21])[NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 867063206-Bromo-2-(diethoxymethyl)-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 867063196-Bromo-2-(diethoxymethyl)-1H-pyrrolo[3,2-c]pyridineYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

6-Bromo-2-(diethoxymethyl)-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridine (Preparation 136, 202 mg, 0.54 mmole) was stirred in methanol (2.4 mL) and 1M sodium hydroxide in water (0.62 mL, 0.62 mmole) was added. The reaction was stirred at 25° C. for 6 hours. The methanol was evaporated and the residue taken up in ethyl acetate (25 mL). The solution was washed with water and brine, the organic layer was concentrated in vacuo to afford the title compound (142 mg, 89%). 1H-NMR (CDCl3, 500 MHz): δ 1.27 (t, J=6.94 Hz, 6H), 3.58-3.72 (m, 4H), 5.73 (m, 1H), 6.59 (m, 1H), 7.48 (m, 1H), 8.65 (s, 1H), 8.84 (br s, 1H, NH).

Workup

  1. customThe methanol was evaporated
  2. washThe solution was washed with water and brine
  3. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-60429d4e27f541e29bf4d18a7dfd7d7f
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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