Water → HCID 57537530, compound

HRID 1693717Notes

Reaction equation

HRID 1693717 reaction equation
[N:1]([C:4]1[C:9]([Br:10])=[CH:8][N:7]=[C:6]2[N:11]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:12]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[C:5]=12)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[Br:10][C:9]1[C:4]([NH2:1])=[C:5]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])=[CH:12][N:11]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:6]2=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 11776TriphenylphosphineHCID 57537607HCID 57537607, compound

Product 1

HCID 57537530HCID 57537530, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

4-Azido-5-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (115 mg, 0.24 mmol), triphenylphosphine (64 mg, 0.24 mmol), and water (44 μL, 2.4 mmol) were dissolved in tetrahydrofuran (1 mL). The reaction was stirred at 23° C. for 1 h. Water (100 μL, 5.5 mmol) was added and the mixture was stirred an additional 14 h. The reaction mixture was directly loaded onto silica gel and purified using flash silica gel chromatography using a gradient of (ethyl acetate and methanol 9:1) in hexanes to afford 5-Bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-ylamine (MS: m/z 448.1/450.1 (M+H+).

Workup

  1. stirringthe mixture was stirred an additional 14 h
  2. custompurified

Sources & evidence

ORD record
ord-d0a096b3b7a04e4d888a11c854c3dbd6
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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