Formaldehyde → HCID 59700007, compound

HRID 729810Notes

Reaction equation

HRID 729810 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[NH:11][CH:10]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[CH2:31]=O>CO.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:31][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[C:20]([OH:24])[CH:19]=3)[CH:16]=2)[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 59699737HCID 59699737, compound

Product 1

HCID 59700007HCID 59700007, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenol (14.2 mg, 0.045 mmol), morpholine (5.87 μl, 0.067 mmol) and paraformaldehyde (2.7 mg, 0.09 mmol) in 400 μl of methanol/toluene (3:7) was stirred at 60° C. for 1 hour, then 90° C. for 3 hours. The resulting light brown residue was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-morpholin-4-ylmethyl-phenol (11.7 mg, 63% yield) as white solid. 1H NMR (500 MHz, CD3OD) δ 8.44 (d, 1.5 Hz, 1H), 8.22 (d, 1.5 Hz, 1H), 7.65 (s, 1H), 7.56 (dd, 1.5 Hz, 7 Hz, 1H), 7.37 (d, 8 Hz, 1H), 7.32 (dt, 2 Hz, 7.8 Hz, 1H), 7.19 (dd, 2 Hz, 8 Hz, 1H), 7.17 (d, 1.5 Hz, 1H), 7.14 (d, 8 Hz, 1H), 7.06 (dt, 1 Hz, 7 Hz, 1H), 4.18 (s, 2H), 3.87 (s, 3H), 3.85 (br s, 4H), 3.09 (br s, 4H). MS: m/z 416.1 [MH+].

Workup

  1. wait90° C. for 3 hours
  2. customThe resulting light brown residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-ccc30a96666c457996fee6e9ddef4ca2
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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