Sodium Hydroxide → 4-[3-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]butan-1-ol

HRID 1991131Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:14]=3)[N:9](S(C3C=CC=CC=3)(=O)=O)[CH:8]=2)[CH:4]=[N:3]1.[OH-].[Na+]>CCO.CCOC(C)=O.[Cl-].[Na+].O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:14]=3)[NH:9][CH:8]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

To crude azaindole 66 (76 mg, 0.19 mmol) in EtOH (6 mL) was added 10% NaOH (1 mL) and the mixture was stirred in an oil bath (90° C.) for 2 h. The mixture was then cooled to r.t., diluted with AcOEt and saturated brine and partitioned. The aqueous layer was extracted with AcOEt (3×). The combined organic solutions were dried (MgSO4), filtered and concentrated. The residual yellow oil was purified by means of PTLC employing AcOEt as eluent to afford the azaindole 67 (16 mg, 31%); 1H NMR (400 MHz; CDCl3) δ 1.61-1.80 (m, 8H), 2.77 (t, J=7.6 Hz, 2H), 3.67 (t, J=6.6 Hz, 2H), 3.97 (s, 3H), 7.34 (d, J=1.9 Hz, 1H), 7.61 (s, 1H), 7.73 (d, J=0.6 Hz, 1H), 7.85 (d, J=1.8 Hz, 1H), 8.17 (d, J=1.8 Hz, 1H), 9.29 (br s, 1H).

Workup

temperatureThe mixture was then cooled to r.t.
custompartitioned
extractionThe aqueous layer was extracted with AcOEt (3×)
dry with materialThe combined organic solutions were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residual yellow oil was purified by means of PTLC

Sources & evidence

ORD record: ord-ce68c7bb760a41baa68552a58082f190
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645769B2

Reaction notes

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