Dichloromethane → HCID 76284887, compound

HRID 1778727Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19](I)=[N:20][NH:21][C:15]=2[CH:14]=1.CC1(C)C(C)(C)OB([C:31]2[CH:32]=[N:33][N:34]([CH2:36][C@@H:37]([OH:39])[CH3:38])[CH:35]=2)O1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19]([C:31]3[CH:32]=[N:33][N:34]([CH2:36][C@@H:37]([OH:39])[CH3:38])[CH:35]=3)=[N:20][NH:21][C:15]=2[CH:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine (15 mg, 0.033 mmol) (Example 28, Step 4), (2S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol (10 mg, 0.04 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complexed with dichloromethane (1:1) (2 mg, 0.003 mmol), and potassium phosphate (14 mg, 0.067 mmol) in 1,4-dioxane (0.3 mL) and water (0.05 mL) in a reaction vial was degassed and sealed. It was stirred at 90° C. overnight. After cooling it was diluted with methanol, purified by RP-HPLC (pH=2) to afford the desired product (2.5 mg) as TFA salt. LCMS (M+H)+=448.1.

Workup

customvial was degassed
customsealed
temperatureAfter cooling it
additionwas diluted with methanol
custompurified by RP-HPLC (pH=2)

Sources & evidence

ORD record: ord-f4303696982f457c8b665477d819202e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266892B2

Reaction notes

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