Ethanol → [1-(6'-Benzyloxy-[3,3']bipyridinyl-6-yl)-cyclopropyl]-carbamic acid tert-butyl ester

HRID 2038794Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14](I)=[CH:13][N:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][N:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CCO>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[N:12]=[CH:13][C:14]([C:30]3[CH:29]=[N:28][C:27]([O:26][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:32][CH:31]=3)=[CH:15][CH:16]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of [1-(5-iodo-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (0.25 g, 0.69 mmol) in DME (1 mL) was added PdCl2(dppf).dichloromethane complex (57 mg, 0.07 mmol). This solution was transferred to a microwave vial containing 2-benzyloxypyridine-5-boronic acid (0.17 g, 0.76 mmol) and K3PO4 (1M, 0.90 mL, 0.90 mmol). Water (0.4 mL) and EtOH (0.3 mL) were added and the mixture heated in a microwave at 100° C. for 10 minutes. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined extracts were washed with water, brine and dried with MgSO4. The mixture was filtered and concentrated to give [1-(6′-benzyloxy-[3,3′]bipyridinyl-6-yl)-cyclopropyl]-carbamic acid tert-butyl ester (0.24 g, 0.58 mmol) as a brown solid, m/z 418.8 [M+H]+.

Workup

extractionextracted with EtOAc (3×50 mL)
washThe combined extracts were washed with water, brine
dry with materialdried with MgSO4
filtrationThe mixture was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-79dbaea845f0473f86b99c3d1205285a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575360B2

Reaction notes

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