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3-Bromopyridine → HCID 69550697, compound

HRID 348552
Notes
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Reaction equation

HRID 348552 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=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.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.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(OCC)C>[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:3]=[N:4][CH:5]=[CH:6][CH:7]=3)[CH2:22][CH2:21]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 122863-Bromopyridine2×HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 86594093HCID 86594093, compound

Product 1

HCID 69550697HCID 69550697, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 1140
Toluene
Solvent
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 3-bromo-pyridine as follows: A suspension of (+/−)-[cis-1-(2-phenyl-cyclohexyl)-piperidin-4-yl]-amine (1.00 g, 3.88 mmol) in toluene (30 ml) was degassed with a flow of argon for 10 minutes. Tris-(dibenzylideneacetone)dipalladium chloroform complex (124 mg, 0.12 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (BINAP, 76.0 mg, 0.12 mmol), sodium tert-butoxide (0.470 g, 4.89 mmol) and 3-bromopyridine (0.483 g, 3.06 mmol) were added under argon. The flask was sealed and warmed to 70° C. for 3 hours. The mixture was diluted with ethyl acetate (30 ml) and diethyl ether (30 ml) and washed three times with saturated sodium chloride solution. The organic phase was dried with sodium sulphate and evaporated, yielding a red oil. Purification was achieved by flash chromatography (dichloromethane/methanol/25% NH3 90:10:1). (+/−)-[cis-1-(2-Phenyl-cyclohexyl)-piperidin-4-yl]-pyridin-3-yl-amine (0.260 g, 20%) was obtained as an orange 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 a red oil
  7. customPurification

Sources & evidence

ORD record
ord-17ff4505d760488d93c2e967de338844
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