6-(4-Fluoro-phenyl)-3-iodo-pyrazolo[1,5-a]pyridine → HCID 24962177, compound

HRID 1894191Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3I)[CH:13]=2)=[CH:4][CH:3]=1.[S:18]1[CH:22]=[N:21][N:20]=[C:19]1[NH:23][C:24]1[CH:25]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:27]=[CH:28][CH:29]=1>COCCOC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:26]3[CH:25]=[C:24]([NH:23][C:19]4[S:18][CH:22]=[N:21][N:20]=4)[CH:29]=[CH:28][CH:27]=3)[CH:13]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-(4-fluoro-phenyl)-3-iodo-pyrazolo[1,5-a]pyridine (150 mg, 0.44 mmol), 3-([1,3,4]thiadiazol-2-ylamino)-phenyl boronic acid pinacol ester (190 mg, 0.62 mmol) and PdCl2ddpf (32 mg, 0.04 mmol) in DME (1.5 ml) and 2N Na2CO3 (aq, 1.5 ml) in a microwave vial was deoxygenated by bubbling N2 through for 30 seconds. The vial was sealed and then stirred and heated at 150° C. in the microwave for 30 minutes. After cooling to RT the mixture was partitioned between CH2Cl2/H2O. The organic layer was evaporated and the residue was purified by preparative HPLC to give the title compound (15 mg, solid).

Workup

custom2N Na2CO3 (aq, 1.5 ml) in a microwave vial was deoxygenated
customby bubbling N2 through for 30 seconds
customThe vial was sealed
temperatureAfter cooling to RT the mixture
customwas partitioned between CH2Cl2/H2O
customThe organic layer was evaporated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-f3f71754fefd4862ae5ca24bfecd57f4
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513276B2

Reaction notes

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