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Diphenylmethylidenehydrazine → N-Benzhydrylidene-N'-(5-fluoro-3-methyl-pyridin-2-yl)-hydrazine

HRID 2285169
Notes
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Reaction equation

HRID 2285169 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.[C:10](=[N:23][NH2:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.C1(B(O)O)C=CC=CC=1>[C:10](=[N:23][NH:24][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 79304DiphenylmethylidenehydrazineHCID 23665647Potassium tert-butoxideHCID 248203202-Bromo-5-fluoro-3-methylpyridine

Product 1

HCID 86687171N-Benzhydrylidene-N'-(5-fluoro-3-methyl-pyridin-2-yl)-hydrazineYield 64.2%

Reagents, catalysts & solvents 2

HCID 66827Phenylboronic AcidCatalyst
HCID 1140
Toluene
Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-5-fluoro-3-methyl-pyridine (190 mg, 1.0 mmol), benzhydrylidene-hydrazine (216 mg, 1.1 mmol), phenylboronic acid (5 mol %, 6 mg) and potassium tert-butoxide (157 mg, 1.4 mmol) in anhydrous toluene (6 mL) was degassed with a stream of argon, treated with Pd(OAc)2 (2 mol %, 5 mg) and racemic (1,1′-binaphthalene-2,2′-diyl)bis(diphenylphosphine) (2 mol %, 12 mg) and stirred at 80° C. for 1 h. After cooling to RT, the reaction mixture was diluted with EtOAc and washed with water followed by a saturated aqueous solution of NaHCO3. The organic layer was dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by FCC on silica, using a gradient of 1-10% MeOH in DCM followed by 100% DCM, to afford the title compound (196 mg, 64%). LCMS (Method 4): Rt 3.44 min, m/z 306 [MH+].

Workup

  1. customwas degassed with a stream of argon
  2. additiontreated with Pd(OAc)2 (2 mol %, 5 mg) and racemic (1,1′-binaphthalene-2,2′-diyl)bis(diphenylphosphine) (2 mol %, 12 mg)
  3. temperatureAfter cooling to RT
  4. additionthe reaction mixture was diluted with EtOAc
  5. washwashed with water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by FCC on silica

Sources & evidence

ORD record
ord-f149bc3a91dc489a947e7dcb29aad16e
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145413B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes