Hydrochloric Acid → HCID 58824205, compound

HRID 490353Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([CH3:27])=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:14][CH:13]=2)[CH:9]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].I[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][N:36]=1.O=O.Cl>O1CCOCC1.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]>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([CH3:27])=[C:8]([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][N:36]=3)=[CH:16][CH:17]=2)[CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester (51) (126 mg), 2M aqueous cesium carbonate (0.6 mL) and 2-iodo-5-methoxypyridine (95 mg) in 1,4-dioxan (10 mL) under an argon atmosphere was sonicated to expel traces of oxygen. [1,1′-Bis-(diphenylphosphino) ferrocene]dichloropalladium (II) (8 mg) was added and the mixture heated at 95° C. for 18 hours. After cooling, the mixture was acidified to pH6 with 1M aqueous hydrochloric acid and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give compound 52 as an oil (70 mg), which was used directly in the next step. LC/MS System A: Rt=3.23 mins, m/z=354 ((M+H) for C20H19NO5).

Workup

customwas sonicated
temperatureAfter cooling
custompartitioned between ethyl acetate and water
dry with materialThe organic phase was dried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-6e3e81969e774875a9446bdb9ced16be
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528157B2

Reaction notes

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