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4-Bromopyridine → HCID 86594094, compound

HRID 348553
Notes
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Reaction equation

HRID 348553 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:8]1([C@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[N:20]2[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(C)([O-])C.[Na+].Cl.BrC1C=CN=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:8]1([C@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[N:20]2[CH2:25][CH2:24][CH:23]([NH:26][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[CH2:22][CH2:21]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 142684-BromopyridineHCID 881004-Bromopyridinium chlorideHCID 23676156Sodium t-butoxideHCID 86594093HCID 86594093, compound

Product 1

HCID 86594094HCID 86594094, compoundYield 47%

Reagents, catalysts & solvents 5

HCID 167845
palladium(II) acetate
Catalyst
HCID 634876Binap, (A+-)-Catalyst
HCID 1140TolueneSolvent
HCID 3283Diethyl EtherSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

The title compound, MS (ISP): m/e=440.4 (M+H+), was prepared as for example 209, steps (A) to (C). Step (B) was performed using 4-bromo-pyridine as follows: A suspension of (+/−)-[cis-1-(2-phenyl-cyclohexyl)-piperidin-4-yl]-amine (0.303 g, 1.17 mmol) in toluene (10 ml) was degassed with a flow of argon for 10 minutes. Palladium(II) acetate (8.0 mg, 0.036 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (BINAP, 23.0 mg, 0.037 mmol), sodium tert-butoxide (0.280 g, 2.91 mmol) and 4-bromopyridine hydrochloride (0.194 g, 1.00 mmol) were added under argon. The flask was sealed and warmed to 70° C. for 3 hours. The mixture was diluted with ethyl acetate (10 ml) and diethyl ether (10 ml) and washed three times with saturated sodium chloride solution. The organic phase was dried with sodium sulphate and evaporated, yielding an orange oil. Purification was achieved by flash chromatography (dichloromethane/methanol/25% NH3 65:10:1). (+/−)-[cis-1-(2-Phenyl-cyclohexyl)-piperidin-4-yl]-pyridin-4-yl-amine (0.187 g, 47%) was obtained as a light yellow foam, MS (ISP): m/e=336.3 (M+H+). This was reacted with benzoyl chloride in step (C).

Workup

  1. customwas degassed with a flow of argon for 10 minutes
  2. customThe flask was sealed
  3. washwashed three times with saturated sodium chloride solution
  4. dry with materialThe organic phase was dried with sodium sulphate
  5. customevaporated
  6. customyielding an orange oil
  7. customPurification

Sources & evidence

ORD record
ord-348f286791744751807bb7f4761d0fd0
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07176316B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes