Sodium Carbonate → HCID 66970976, compound

HRID 1361520Notes

Reaction equation

HRID 1361520 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl.[C@@H:8]12[CH2:14][C@@H:11]([CH2:12][CH2:13]1)[CH2:10][C@H:9]2[N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[C:25](Br)[CH:24]=[CH:23][C:22]=2[O:28][CH3:29])[CH2:17][CH2:16]1.CC1(C)C(C)(C)OB([C:38]2[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=2)O1>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].C(#N)C>[C@@H:8]12[CH2:14][C@@H:11]([CH2:12][CH2:13]1)[CH2:10][C@H:9]2[N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[C:25]([C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)[CH:24]=[CH:23][C:22]=2[O:28][CH3:29])[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 66970673HCID 66970673, compound

Product 1

HCID 66970976HCID 66970976, compound

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 6342AcetonitrileSolvent

Procedure

Dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium(II)dichloromethane adduct (12 mg, 0.015 mmol), acetonitrile (500 μL), 2.0 M sodium carbonate (aq) (250 μL), 1-((1S,2R,4R)-bicyclo[2.2.1]heptan-2-yl)-4-(5-bromo-2-methoxyphenyl)piperidine hydrochloride (compound no. 187) (60 mg, 0.15 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (31 mg, 0.15 mmol) were combined in a microwave vial. The vial was flushed with nitrogen, capped and microwaved at 140° C. for 20 min. The reaction was diluted with methanol (750 μL), mixed well and then filtered (Whatman 0.20 μM PTFE) and subjected to reverse-phase HPLC purification (2-40% CH3CN/0.08% TFA) to yield [4-(3-(1-((1S,2R,4R)-bicyclo[2.2.1]heptan-2-yl)piperidin-4-yl)-4-methoxyphenyl) pyridine] (compound no. 124) as the TFA salt. LC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 363.4 [M+H]+, retention time 1.67 min.

Workup

  1. customThe vial was flushed with nitrogen
  2. customcapped
  3. custommicrowaved at 140° C. for 20 min
  4. additionThe reaction was diluted with methanol (750 μL)
  5. additionmixed well
  6. filtrationfiltered (Whatman 0.20 μM PTFE)
  7. customsubjected to reverse-phase HPLC purification (2-40% CH3CN/0.08% TFA) to yield [4-(3-(1-((1S,2R,4R)-bicyclo[2.2.1]heptan-2-yl)piperidin-4-yl)-4-methoxyphenyl) pyridine] (compound no. 124) as the TFA salt
  8. customLC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 363.4 [M+H]+, retention time 1.67 min.

Sources & evidence

ORD record
ord-ccc13b25f95d4cdf84573eacfee5798f
Source dataset
uspto-grants-2011_02
Patent number
US07880007B2

Reaction notes

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