2-Bromo-5-(trifluoromethyl)-1,3,4-thiadiazole → HCID 73335799, compound

HRID 925800Notes

Reaction equation

HRID 925800 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]([C:32]([F:35])([F:34])[F:33])=[N:30][N:31]=1>>[F:1][C:2]1[CH:10]=[C:9]([C:27]2[S:28][C:29]([C:32]([F:35])([F:34])[F:33])=[N:30][N:31]=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 128746852-Bromo-5-(trifluoromethyl)-1,3,4-thiadiazoleHCID 90036316HCID 90036316, compound

Product 1

HCID 73335799HCID 73335799, compound

Procedure

The title compound, light yellow solid (10 mg, 14%), MS (ISP) m/z=371.5 [(M+H)+], mp 227° 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-trifluoromethyl-1,3,4-thiadiazole (69.9 mg, 0.3 mmol).

Sources & evidence

ORD record
ord-a9b58828f62e40968b22ee83b5268d88
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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