Potassium Phosphate, Tribasic → 2-(5-(3-Cyclopropylpyrazolo[1,5-a]pyridin-2-yl)pyridin-3-yl)propan-2-ol

HRID 530018Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:15]([OH:18])([CH3:17])[CH3:16])[CH:12]=[N:13][CH:14]=2)O1.Cl[C:21]1[C:29]([CH:30]2[CH2:32][CH2:31]2)=[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]2[N:22]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:30]1([C:29]2[C:21]([C:9]3[CH:10]=[C:11]([C:15]([OH:18])([CH3:16])[CH3:17])[CH:12]=[N:13][CH:14]=3)=[N:22][N:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=23)[CH2:32][CH2:31]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the title compound from Example 1 Step D (0.114 g, 0.434 mmol) and the title compound from Example 1 Step B (0.084 g, 0.434 mmol) in tetrahydrofuran (4.34 mL) were added palladium acetate (0.010 g, 0.043 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.036 g, 0.087 mmol), and potassium phosphate tribasic (0.277 g, 1.30 mmol). The resulting mixture was heated at 100° C. for 18 hours, then filtered and concentrated under reduced pressure. Purification by column chromatography on silica gel (0-25% ethyl acetate in hexanes) provided the title compound: LCMS m/z 293.86 [M+H]+; 1H NMR (500 MHz, CDCl3) 9.16 (s, 1H), 8.76 (s, 1 H), 8.45 (dd, J=2.0, 2.0 Hz, 1 H), 7.66 (d, J=8.8 Hz, 1 H), 7.11 (d, J=6.9 Hz, 1 H), 6.75 (dd, J=6.7, 6.7 Hz, 1 H), 2.45 (br s, 1 H), 2.01-1.98 (m, 1 H), 1.68 (s, 6 H), 1.01 (d, J=8.0 Hz, 2 H), 0.50 (d, J=5.0 Hz, 2 H).

Workup

filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by column chromatography on silica gel (0-25% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-953840ba03614e3f97a49794873e7ba0
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09351973B2

Reaction notes

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