HCID 71059681, compound → HCID 71059532, compound

HRID 1425601Notes

Reaction equation

HRID 1425601 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[N+:17]([O-])=O)=[CH:7][CH:6]=1>P(OCC)(OCC)(OCC)=O>[F:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]2[C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:16]=3[NH:17][C:7]=2[CH:6]=1

Participants

3

Reactant 1

HCID 71059681HCID 71059681, compound

Product 1

HCID 71059532HCID 71059532, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6535Triethyl PhosphateSolvent

Procedure

A solution of 3-(4-(3-fluoropropyl)phenyl)-4-nitropyridine (12 mg, 0.046 mmol) in 0.3 mL of triethyl phosphate was heated at 125° C. for 1 h. After cooling to rt, the volatiles were removed under reduced pressure and the residue was purified by silica chromatography (MeOH in DCM, 0% to 10%) to afford a off-white solid. This material was then further purified by reversed phase HPLC to yield 7-(3-fluoropropyl)-5H-pyrido[4,3-b]indole as a white solid (3 mg, 28%). 1H NMR (400 MHz, methanol-d4): δ 9.15 (s, 1H), 8.32 (d, J=4.4, 1H), 8.07 (d, J=8.0 Hz, 1H), 7.44 (d, J=6 Hz, 1H), 7.37 (m, 1H), 7.16 (dd, J=8.0, 1.2 Hz, 1H), 4.50 (t, J=6 Hz, 1H), 4.43 (t, J=6 Hz, 1H), 2.90 (t, J=7.6 Hz, 2H), 2.12-1.99 (m, 2H); MS (ESI) m/z [M+H]+229.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customthe residue was purified by silica chromatography (MeOH in DCM, 0% to 10%)
  3. customto afford a off-white solid
  4. customThis material was then further purified by reversed phase HPLC

Sources & evidence

ORD record
ord-df64ce6adfea496db71bc013575e9401
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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