2-Bromo-5-chlorothiophene → HCID 73335798, compound

HRID 925799Notes

Reaction equation

HRID 925799 reaction equation
[F:1][C:2]1[CH:10]=[C:9](B2OC(C)(C)C(C)(C)O2)[C:8]2[N:7]3[CH2:20][CH2:21][NH:22][C:23](=[O:24])[C:6]3=[C:5]([CH3:25])[C:4]=2[CH:3]=1.Br[C:27]1[S:28][C:29]([Cl:32])=[CH:30][CH:31]=1>>[Cl:32][C:29]1[S:28][C:27]([C:9]2[C:8]3[N:7]4[CH2:20][CH2:21][NH:22][C:23](=[O:24])[C:6]4=[C:5]([CH3:25])[C:4]=3[CH:3]=[C:2]([F:1])[CH:10]=2)=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 761332-Bromo-5-chlorothiopheneHCID 90036316HCID 90036316, compound

Product 1

HCID 73335798HCID 73335798, compound

Procedure

The title compound, light brown solid (15 mg, 22%), MS (ISP) m/z=335.4 [(M+H)+], mp 185° C., was prepared in accordance with the general method of example 171, step B from 8-fluoro-10-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (Example 171, step A) (68.8 mg, 0.2 mmol) and commercially available 2-bromo-5-chlorothiophene (59.2 mg, 0.3 mmol).

Sources & evidence

ORD record
ord-17c425cfcd14497a815773164e14a176
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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