Ethyl formate → 3-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-azetidine-1-carbaldehyde

HRID 2046932Notes

Reaction equation

HRID 2046932 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]4[C:18]([CH:19]([C:21]5[C:26]([Cl:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=5[Cl:29])[CH3:20])=[CH:17][NH:16][C:13]4=[N:14][CH:15]=3)[CH:7]=[N:6]2)[CH2:2]1.[CH:30](OCC)=[O:31]>>[Cl:29][C:22]1[C:23]([F:28])=[CH:24][CH:25]=[C:26]([Cl:27])[C:21]=1[CH:19]([C:18]1[C:12]2[C:13](=[N:14][CH:15]=[C:10]([C:8]3[CH:7]=[N:6][N:5]([CH:3]4[CH2:2][N:1]([CH:30]=[O:31])[CH2:4]4)[CH:9]=3)[CH:11]=2)[NH:16][CH:17]=1)[CH3:20]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 462154755-(1-azetidin-3-yl-1H-pyrazol-4-yl)-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 866574943-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-azetidine-1-carbaldehyde

Conditions

Temperature
50 °C

Procedure

A mixture of 5-(1-azetidin-3-yl-1H-pyrazol-4-yl)-3-[1-(2,6-dichloro-3-fluorophenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (6.0 mg, 0.014 mmol) and ethyl formate (2 mL) was heated to 50° C. overnight in a sealed tube. The solution was concentrated in vacuo, redissolved in MeOH and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.89 (d, J=7.3 Hz, 3 H), 4.37 (ddd, J=6.2, 5.1, 4.9 Hz, 1 H), 4.46-4.54 (m, 1 H), 4.60 (dd, J=9.2, 5.4 Hz, 1 H), 4.71 (t, J=8.6 Hz, 1 H), 5.30 (q, J=7.3 Hz, 1 H), 5.38 (tt, J=8.2, 5.5 Hz, 1 H), 7.16-7.23 (m, 1 H), 7.38 (d, J=1.3 Hz, 1 H), 7.39-7.57 (m, 2 H), 7.72 (s, 1 H), 7.95 (s, 1 H), 8.07 (s, 1 H), 8.33 (d, J=1.8 Hz, 1 H). MS (ES+): m/z 458.06 (100) [MH+]. HPLC: tR=3.22 min (ZQ3, polar—5 min).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionredissolved in MeOH
  3. custompurified via HPLC
  4. additionThe fractions containing the pure product
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-073e850bc40a499d973e873e6e595716
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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