Methanol → HCID 57477670, compound

HRID 1426558Notes

Reaction equation

HRID 1426558 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][C:3]=12.[NH2:19][NH2:20].CO>>[NH:19]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][C:3]=12)[NH2:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 574775614-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57477670HCID 57477670, compoundYield 92%

Conditions

Temperature
97 °C

Procedure

To 4-bromo-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine (1.98 g, 0.00605 mol) was added hydrazine (11.0 mL, 0.350 mol) followed by addition of methanol (1.0 mL, 0.025 mol) (to improve solubility). The reaction mixture was heated in a sealed tube at 97° C. (an oil bath) for 18 h. The reaction mixture was cooled to rt and formed an off-white solid precipitate. The solid was filtered off and rinsed with cold water and dried to give 4-hydrazino-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine (1.55 gm) as a light yellow solid, LC/MS (M+H)+:279, 1H NMR (DMSO-d6) δ 7.98(d, 1H), 7.91(s, 1H), 7.28(d, 1H), 6.69(s, 1H), 6.61(d, 1H), 5.58(s, 2H), 4.37(s, 2H), 3.56(t, 2H), 0.90(t, 2H), 0.0(s, 9H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customformed an off-white solid precipitate
  3. filtrationThe solid was filtered off
  4. washrinsed with cold water
  5. customdried

Sources & evidence

ORD record
ord-fc04ebb53c994f658417e867cb7a9492
Source dataset
uspto-grants-2015_01
Patent number
US08933086B2

Reaction notes

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