4-Vinylpyridine → HCID 66661704, compound

HRID 969100Notes

Reaction equation

HRID 969100 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH2:16][C@@:15]4([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=5[C:19](=[O:26])[O:18]4)[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:27]([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)=[CH2:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:32]1[CH:33]=[CH:34][C:29](/[CH:27]=[CH:28]/[C:2]2[CH:7]=[CH:6][C:5]([C:8]3([C:11]([N:13]4[CH2:17][CH2:16][C@@:15]5([C:21]6[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=6[C:19](=[O:26])[O:18]5)[CH2:14]4)=[O:12])[CH2:9][CH2:10]3)=[CH:4][CH:3]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 75024-VinylpyridineHCID 11430Potassium CarbonateHCID 66661876(1R)-1'-{[1-(4-bromophenyl)cyclopropyl]-carbonyl}-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

Product 1

HCID 66661704HCID 66661704, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of POPd1 catalyst (CombiPhos Catalysts, Inc) (2 mg), (1R)-1′-{[1-(4-bromophenyl)cyclopropyl]-carbonyl}-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (15 mg, 0.036 mmol), 4-vinylpyridine (19 mg, 0.18 mmol), potassium carbonate (5.5 mg, 0.04 mmol) in N,N-dimethylformamide (0.3 ml) was microwave irradiated at 135° C. for 30 minutes. Then the desired product was obtained from the mixture by prep-HPLC followe by chiral HPLC (13 mg, 82%). LCMS: m/z 437.2 (M+H)+; 459.2 (M+Na)+.

Workup

  1. customwas microwave irradiated at 135° C. for 30 minutes

Sources & evidence

ORD record
ord-acc024e2dea74bc3807ae14e39eedc5d
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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