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2-(Di-tert-butylphosphino)biphenyl → HCID 86659376, compound

HRID 1187673
Notes
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Reaction equation

HRID 1187673 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=2)[CH:5]=[C:4]([Cl:14])[N:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]([NH2:24])[CH3:23])=[CH:18][CH:17]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[Cl:14][C:4]1[N:3]=[C:2]([NH:24][C@H:22]([C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)[CH3:23])[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=2)[CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 23676156Sodium t-butoxideHCID 866593752,6-Dichloro-4-(1-methyl-1H-pyrazol-4-yl)pyridine

Product 1

HCID 86659376HCID 86659376, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

257 mg of 2,6-dichloro-4-(1-methyl-1H-pyrazol-4-yl)pyridine obtained by Step 1, 164 mg of (S)-(−)-1-(4-fluorophenyl)ethylamine, 66 mg of 2-(di-t-butylphosphino)biphenyl, 271 mg of sodium t-butoxide and 25 mg of palladium acetate were added in turn to 6 ml of degassed toluene, and the mixture was stirred at 85° C. for 2 hours under argon atmosphere. The reaction solution was purified by silica gel column chromatography to obtain 240 mg of the objective compound as pale yellow powder.

Workup

  1. customThe reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e5f4864e183b43db84331750e44588fc
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673891B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes