2-Bromopyridine → HCID 66700973, compound

HRID 1253687Notes

Reaction equation

HRID 1253687 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[N:8]1[CH2:7][CH2:6][C:5]2([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]2)[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 634876Binap, (A+-)-HCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

Product 1

HCID 66700973HCID 66700973, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Sodium t-butylate (5.4 mmol, 3.0 eq.) was added to a stirred mixture of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (1.8 mmol, 1.0 eq.) and 2-bromopyridine (1.8 mmol, 1.0 eq.) in toluene (30 ml) and the reaction mixture was degassed with N2 for 15-20 min. BINAP (0.108 mmol, 0.06 eq.) and Pd(OAc)2 (0.036 mmol, 0.02 eq.) were added and the reaction mixture obtained is heated at 120° C. for 12 h. The reaction mixture was filtered over Celite and the filtrate was concentrated in vacuo in order to obtain the crude product, which was purified by column chromatography (silica gel, 30% ethyl acetate in hexane). Yield: 69%

Workup

  1. customthe reaction mixture was degassed with N2 for 15-20 min
  2. customthe reaction mixture obtained
  3. filtrationThe reaction mixture was filtered over Celite
  4. concentrationthe filtrate was concentrated in vacuo in order

Sources & evidence

ORD record
ord-db75af8762634b789f7e7cd36f85876a
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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