Dichloromethane → HCID 66668307, compound

HRID 1186816Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:13]2=[N:14][CH:15]=[CH:16][C:17](I)=[C:12]2[CH:11]=[N:10]1.CC1(C)C(C)(C)[O:23][B:22](B2OC(C)(C)C(C)(C)O2)[O:21]1.C([O-])(=O)C.[K+].C(Cl)Cl>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:13]2=[N:14][CH:15]=[CH:16][C:17]([B:22]([OH:23])[OH:21])=[C:12]2[CH:11]=[N:10]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a 48 mL pressure bottle containing Intermediate 74A (1.19 g, 3.24 mmol) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.35 g, 13.86 mmol), potassium acetate (1.36 g, 13.86 mmol), and anhydrous DMSO (12.5 mL). The reaction mixture was purged with argon and treated with PdCl2(dppf).CH2Cl2 (56 mg, 0.077 mmol). The reaction mixture was heated to 85° C. for 1 h, then at 105° C. for 1 h to give conversion to the desired product. LC/MS (Condition B): ret. T=2.7 min, (M+H)+ 276.01.

Workup

customThe reaction mixture was purged with argon
additiontreated with PdCl2(dppf)

Sources & evidence

ORD record: ord-e5cfe50cdc6541528b1a501cdf903b8d
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673922B2

Reaction notes

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