Sodium Carbonate → HCID 59543413, compound

HRID 1798937Notes

Reaction equation

C(OC([N:8]1[CH:13]=[C:12](Br)[CH:11]=[CH:10][CH:9]1[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=O)(C)(C)C.[N:21]1([C:27]2[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[C:36]([O-:39])([O-])=[O:37].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(#N)C>[C:15]([O:39][C:36]([N:18]1[CH2:17][CH2:16][CH:15]([C:9]2[CH:10]=[CH:11][C:12]([C:30]3[CH:31]=[CH:32][C:27]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:28][CH:29]=3)=[CH:13][N:8]=2)[CH2:20][CH2:19]1)=[O:37])([CH3:20])([CH3:16])[CH3:9]

Participants

Conditions

Temperature: 85 °C

Procedure

5-Bromo-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1-carboxylic acid tert-butyl ester (0.6 g, 1.8 mmol), 4-morpholinylphenylboronic acid (400 mg, 1.9 mmol), bis(triphenylphosphine)-palladium(II)chloride (0.06 g, 0.09 mmol), 1 M Na2CO3 (4 ml) and acetonitrile (4 ml) were mixed in a 5 mL microwave vial. The reaction mixture was heated 1500 sec at 85° C. The water layer was removed. The acetonitrile phase was filtered and evaporated. The remainder was purified on a silicagel column with heptane: EtOAc (1:1) as eluent. 730 mg (98%) was isolated as the free base.

Workup

customThe water layer was removed
filtrationThe acetonitrile phase was filtered
customevaporated
customThe remainder was purified on a silicagel column with heptane: EtOAc (1:1) as eluent
custom730 mg (98%) was isolated as the free base

Sources & evidence

ORD record: ord-cf9ee370204f4e518036a59506508776
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344001B2

Reaction notes

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