2-Bromo-1-fluoro-4-(methylsulfonyl)benzene → 8-(2-Fluoro-5-methylsulfonylphenyl)-6-methylpyrido[4,3-d]pyrimidin-5-one

HRID 575701Notes

Reaction equation

HRID 575701 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[F:12].BrC1C=C(S(CC)(=O)=O)C=CC=1OCCC.FC1C=CC(S(C)(=O)=O)=CC=1B1OC(C)(C)C(C)(C)O1.Br[C:50]1[C:55]2[N:56]=[CH:57][N:58]=[CH:59][C:54]=2[C:53](=[O:60])[N:52]([CH3:61])[CH:51]=1>>[F:12][C:3]1[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=1[C:50]1[C:55]2[N:56]=[CH:57][N:58]=[CH:59][C:54]=2[C:53](=[O:60])[N:52]([CH3:61])[CH:51]=1

Participants

5

Reactant 4

HCID 673870812-Bromo-1-fluoro-4-(methylsulfonyl)benzeneHCID 904163822-(2-Fluoro-5-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 1180219268-Bromo-6-methylpyrido[4,3-d]pyrimidin-5(6H)-oneHCID 1180220082-Bromo-4-ethylsulfonyl-1-propoxybenzene

Product 1

HCID 1180224518-(2-Fluoro-5-methylsulfonylphenyl)-6-methylpyrido[4,3-d]pyrimidin-5-one

Procedure

2-bromo-1-fluoro-4-methylsulfonylbenzene was substituted for the title compound of Example 225, step 1 and was converted to 2-(2-fluoro-5-methylsulfonylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in a manner similar to Example 225, step 2 and then reacted with the title compound of Example 231, step 3 in a manner similar to Example 231, step 4. LCMS: 333.9 (M+H)+.

Sources & evidence

ORD record
ord-c05f599a8118475ea2489abb9f168ee8
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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