5-Bromothiophene-2-carbonitrile → HCID 73335800, compound

HRID 925801Notes

Reaction equation

HRID 925801 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:31][C:30]([C:32]#[N:33])=[CH:29][CH:28]=1>>[F:1][C:2]1[CH:10]=[C:9]([C:27]2[S:31][C:30]([C:32]#[N:33])=[CH:29][CH:28]=2)[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

Participants

3

Reactant 2

HCID 35950595-Bromothiophene-2-carbonitrileHCID 90036316HCID 90036316, compound

Product 1

HCID 73335800HCID 73335800, compound

Procedure

The title compound, light brown solid (25 mg, 38%), MS (ISP) m/z=326.5 [(M+H)+], mp 249° 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 5-bromothiophene-2-carbonitrile (56.4 mg, 0.3 mmol).

Sources & evidence

ORD record
ord-2fee2eb959024bc6b33018825f5bd50c
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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